AU2006200339B2 - Process for preparing 2-chlorothiazole compounds - Google Patents
Process for preparing 2-chlorothiazole compounds Download PDFInfo
- Publication number
- AU2006200339B2 AU2006200339B2 AU2006200339A AU2006200339A AU2006200339B2 AU 2006200339 B2 AU2006200339 B2 AU 2006200339B2 AU 2006200339 A AU2006200339 A AU 2006200339A AU 2006200339 A AU2006200339 A AU 2006200339A AU 2006200339 B2 AU2006200339 B2 AU 2006200339B2
- Authority
- AU
- Australia
- Prior art keywords
- sch
- formula
- compound
- unsubstituted
- cah
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
P/00/011 Regulation 3.2
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT
(ORIGINAL)
Name of Applicant: Actual Inventors: Syngenta Participations AG, of Schwarzwaldallee 215, CH-4058 Basel, SWITZERLAND SZCZEPANSKI, Henry SENN, Marcel GOBEL, Thomas RAPOLD, Thomas HUTER, Ottmar, Franz MAIENFISCH, Peter O'SULLIVAN, Anthony, Cornelius PITTERNA, Thomas Address for Service: DAVIES COLLISON CAVE, Patent Trademark Attorneys, of 1 Nicholson Street, Melbourne, 3000, Victoria, Australia Ph: 03 9254 2777 Fax: 03 9254 2770 Attorney Code: DM Invention Title: "Process for preparing 2-chlorothiazole compounds" The following statement is a full description of this invention, including the best method of performing it known to us:- Process for preparing 2-chlorothiazole compounds This application is a divisional of Australian Patent Application No. 2002300672, the entire contents of which are incorporated herein by reference.
The invention relates to a process for preparing a compound of the formula
X'Y
Cl N Z V
R
i
R
2 in which X is CH or N, Y is NO 2 or CN, Z is CHR 3 O, NR 3 or S, R, and R 2 are either each, independently of the other, hydrogen or unsubstituted or R.
substituted alkyl or together a two- or three-membered alkylene bridge or a two- or three-membered alkylene bridge in which one member is replaced by a hetero member selected from the group, consisting of NRs, O and S,
R
3 is H or unsubstituted or R4-substituted alkyl,
R
4 is an unsubstituted or substituted aryl or heteroaryl group, and Rs is H or alkyl, which comprises a) reacting a compound of the formula (0)n Y R y"z (II), RS J IN R, in which X, Y, Z, R 1 and R 2 are as defined for the formula I, n is 0, 1 or 2, Re is unsubstituted or Re-substituted alkyl, unsubstituted or Re-substituted alkenyl, unsubstituted or Re-substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl, SR 7 (alkylene)SH or (alkylene)SR 7
R
7 is unsubstituted or R4-substituted alkyl, unsubstituted or R 4 -substituted alkenyl, unsubstituted or R4-substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl or a group of the formula -2x-Y R' R2 in which X, Y, Z, R 1 and R 2 are as defined for the formula II, and
R
8 is an unsubstituted or substituted aryl or heteroaryl group, -COOH, COOM, wherein M is an alkali metal, or -COO-C 1 -C-alkyl, with a chlorinating agent, or bl) initially reacting a compound of the formula (O)n S S (IV), N6 in the free form or the form of a salt, in which Re and n are as defined for the formula II and X, is a leaving group, in the presence or absence of a base, with a compound of the formula
X-Y
HN Z I I R,
R
2 which is known or which can be prepared by methods known per se and in which R 1
R
2
X,
Y and Z are as defined for the formula I, and b2) further reacting the compound of the formula II obtainable thereby, with or without intermediate isolation, with a chlorinating agent, to intermediates used in this process, to the use of these intermediates and to a process for the preparation of these intermediates.
The existing processes for preparing the compounds of the formula I require as starting material inter alia 2-chloro-5-chloromethylthiazole. The latter, however, is harmful on direct contact, and there is therefore a need to replace this compound by harmless compounds.
This object is achieved by the preparative process according to the invention.
The general terms used hereinbefore and hereinafter have, unless defined otherwise, the meanings listed below: Carbon-containing groups and compounds each contain, unless defined otherwise, 1 up to and including 8, preferably 1 up to and including 6, in particular 1 up to and including 4, especially 1 or 2 carbon atoms.
Halogen is preferably chlorine or bromine.
Alkyl as a group per se and also as a structural element of other groups and compounds, for example alkoxy and alkylthio is, in each case with due regard to the number of carbon atoms contained in the respective group or compound, either straight-chain, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, for example isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl and alkynyl are straight-chain or branched and each contain two or preferably one unsaturated carbon-carbon bond(s). The double or triple bonds of these substituents are separated from the remainder of the compound II preferably by at least one saturated carbon atom. Examples include allyl, methallyl, but-2-enyl, but-3-enyl, propargyl, but-2-ynyl and but-3-ynyl.
Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl.
Alkylene as a group per se and also as a structural element of other groups and compounds, such as (alkylene)SR 7 is, in each case with due regard to the number of carbon atoms contained in the respective group or compound, either straight-chain, for example -CH 2 CH2, -CH 2
CH
2
CH
2 or -CH 2
CH
2
CH
2
CH
2 or branched, for example -CH(CH 3
-CH(C
2
-C(CH
3 2
CH(CH
3
)CH
2 or -CH(CH 3 )CH(CH3)-, and it can also be methylene.
Aryl is phenyl or naphthyl, in particular phenyl.
Heteroaryl is a 5- to 7-membered aromatic ring with one to up to three hetero atoms selected from the group consisting of N, O and S. Preference is given to aromatic 5- and 6-membered rings which have a nitrogen atom as hetero atom and which can, if desired, also contain a further hetero atom, preferably nitrogen or sulfur, in particular nitrogen.
Substituted aryl and heteroaryl are preferably substitueted with one to three substituents selected from the group consisting of halogen, NO 2 CN, C-C 4 alkyl, C 1
-C
4 alkoxy, halogen-
C
1
-C
4 alkyl and halogenCi-C 4 alkoxy. Preferred are unsubstituted or monosubstituted, especially unsubstituted aryl and heteroaryl.
Preferred starting materials for preparing the corresponding compounds of the formula I according to the invention are: a compound of the formula II where X is N; a compound of the formula II where Y is NO 2 a compound of the formula II where Z is CHR 3 or NR 3 preferably NR 3 a compound of the formula II where
R
1 and R 2 are together a two- or three-membered alkylene bridge with or without a hetero member selected from the group consisting of NRs, O and S; a compound of the formula II where
R
3 is unsubstituted or R 4 -substituted C 1
-C
4 alkyl, preferably unsubstituted C 1
-C
2 alkyl; a compound of the formula II where
R
4 is unsubstituted or substituted aryl or heteroaryl, the substituents being selected from the group consisting of halogen, NO 2 C, C-C 4 alkyl, C 3 -Cecycloalkyl, C 1 -Calkoxy and C 1
C
4 alkylthio, preferably unsubstitued aryl; a compound of the formula II wherein Re is unsubstituted or Rs-substituted C 1
-C
4 alkyl, aryl, heteroaryl, SR 7 (alkylen)SH or (alkylene)SR 7 preferably aryl, Re-substituted C 1
-C
4 alkyl or SR 7 in particular Re-substituted Ci-C 2 alkyl or especially aryl; a compound of the formula II wherein
R
7 is unsubstituted or R 4 -substituted alkyl, aryl, heteroaryl or a group of the formula
X.Y
Sx N
R
RI R2 in which X, Y, Z, Ri and R 2 are as defined for the formula II, in particular a group of the formula III; a compound of the formula II wherein Ra is aryl or heteroaryl, which are either unstubstituted or substituted, the substituents being selected from the group consisting of halogen, NO 2 CN, C 1
-C
4 -alkyl, C 3
-C
cycloalkyl, C 1
-C
4 -alkoxy and C 1
-C
4 -alkylthio; in particular unsubstituted aryl.
Especially preferred according to the invention are the compounds of the formula II mentioned in the Examples.
The reactions described hereinbefore and hereinafter are carried out in a customary manner, for example in the absence or usually in the presence of a suitable solvent or diluent or a mixture thereof, working as the occasion demands with cooling, at room temperature or with heating, for example at a temperature in the range of from about to the boiling point of the reaction medium, preferably at about -20 0 C to about +150 0 C, and, if necessary, in a closed vessel, at elevated pressure, in an inert-gas atmosphere and/or under anhydrous conditions. Especially advantageous reaction conditions are discernible from the Examples.
The starting materials listed hereinbefore and hereinafter used for preparing the compounds I, as the case may be in their free form or as salts, are known or, if they are novel, can be prepared by known methods, for example according to the following specifications.
Variant a) Suitable halogenating agents are for example elemental chlorine, Javelle water, polysulfur dichloride, sulfur dichloride, phosphorus trichloride, phosphorus pentachloride or mixtures of two or more than two of these compounds, preferably elemental chlorine, Javelle water, sulfur dichloride or a mixture of these two compounds, particularly preferably elemental chlorine of Javelle water.
-6- The reaction partners can be reacted with each other without the addition of a solvent or diluent. It may, however, be advantageous to add a solvent or a diluent or a mixture thereof, in which case the amount thereof is not critical. Examples of such solvents or diluents are: water; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetraline, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichloroethene or tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; amides, such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric triamide; nitriles, such as acetonitrile or propionitrile; and sulphoxides, such as dimethyl sulphoxide. The reaction is preferably carried out in the presence of a halogenated hydrocarbon, in particular dichloromethane or chlorobenzene.
The reaction is advantageously carried out at a temperature in the range of from about to about +180 0 C, preferably from about 00C to about +80°C, in many instances in the range between room temperature and the reflux temperature of the reaction mixture.
In a preferred embodiment of variant a compound II is reacted at -10°C to 400C, preferably 0*C, with a chlorinating agent, preferably Javelle water.
The reaction is preferably carried out at atmospheric pressure.
The reaction time is not critical; preference is given to a reaction time of 0.1 to 48 hours, in particular 0.5 to 24 hours.
The product is isolated by customary methods, for example filtration, crystallization, distillation or chromatography or any suitable combination of these procedures.
The yields obtained are generally good.
Variant bl) Suitable leaving groups X 1 in the compounds IV are for example hydroxy, Ci-Cealkoxy, halo- C1-Cealkoxy, C 1 -Csalkanoyloxy, mercapto, C1-Csalkylthio, halo-C 1 -Cealkylthio,
C-C
8 alkanesulfonyloxy, halo-C 1 -Csalkanesulfonyloxy, benzenesulfonyloxy, -7toluenesulfonyloxy and halogen, preferably toluenesulfonyloxy, tri-fluoromethanesulfonyloxy and halogen, in particular halogen.
Bases suitable for facilitating the reaction are for example alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and also carbocyclic amines. Examples are sodium hydroxide, sodium hydride, sodium amide, sodium methanolate, sodium acetate, sodium carbonate, potassium tert-butanolate, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calciumhydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and also 1,5-diazabicyclo[5.4.0]undec-5-ene
(DBU).
The reaction partners can be reacted with each other as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most instances, however, the addition of a solvent or diluent or a mixture thereof is advantageous. Examples of such solvents or diluents are: water; aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetraline, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichloroethene or tetrachloroethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, '.opropanol, butanol, ethylene glycol or glycerol; amides, such as N,N-dimethylformarnide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric triamide; nitriles, such as acetonitrile or propionitrile; and sulphoxides, such as dimethyl sulphoxide. If the reaction is carried out in the presence of a base then bases such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline employed in excess may also serve as solvents or diluents.
The reaction can also be carried out in a heterogeneous two-phase mixture, for example a mixture of an organic solvent and an aqueous solution of a base, if necessary in the presence of a phase-transfer catalyst such as a crown ether or a tetraalkylammonium salt.
The reaction is advantageously carried out at a temperature in the range of from about 00C to about +1 800C, preferably from about +10°C to about +80C, in many instances in the range between room temperature and the reflux temperature of the reaction mixture.
In a preferred embodiment of variant bl), a compound IV is reacted at 00C to 1200C, preferably 200C to 800C, in particular 60"C to 800C, in an amide, preferably N,N-dimethyformamide, with a compound V.
The reaction is preferably carried out at atmospheric pressure.
The reaction time is not critical; preference is given to a reaction time of 0.1 to 48 hours, in particular 0.5 to 24 hours.
The product is isolated by customary methods, for example filtration, crystallization, distillation or chromatography or any suitable combination of these procedures.
The yields obtained are generally good.
Variant b2) Suitable halogenating agents are for example of the kind stated under variant a).
The reaction partners can be reacted with each other as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most instances, however, the addition of a solvent or diluent or a mixture thereof is advantageous. Suitable solvents or diluents are for example of the kind stated under variant a).
The reaction is advantageously carried out at a temperature in the range of from about -200C to about +1800C, preferably from about 00C to about +800C, in many instances between room temperature and the reflux temperature of the reaction mixture.
In a preferred embodiment of variant b2), a compound II is reacted with a chlorinating agent, preferably elermiental chlorine or Javelle water, at -100C to 400C, preferably GIC.
The reaction is preferably carried out at atmospheric pressure.
The reaction time is not critical; preference is given to a reaction time of 0.1 to 48 hours, in particular 0.5 to 24 hours.
The product is isolated by customary methods, for example filtration, crystallization, distillation or chromatography or any suitable combination of these procedures.
The yields obtained are generally good.
Novel starting materials or intermediates, in each case either in their free form or as salts, that are used according to the invention for preparing compounds of the formulae I, II, IV or VII or their salts, respectively, a process for their preparation and their use as starting materials or intermediates for preparing the compounds I, II, IV or VII also form part of the subject-matter of the invention.
The compounds II can be prepared for example as described under variant bl).
Compounds of the formula IV can be prepared for example by reacting a compound of the formula S S (VI),
NH
which is known, with a compound of the formula ReX 2 in which Re has the meanings stated for the formula II and X 2 is a leaving group, and subsequently reacting with a compound of the formula QX, in which Q is an acidic group, for example a preferably inorganic acid function such as in particular SO 2
X
1 and X, has the meanings stated for the formula IV, to give compounds of the formula IV in which n is 0 which can, if desired, be converted further to compounds of the formula IV in which n is 1 or 2 by using an oxidizing agent such as in particular hydrogen peroxide.
The compounds of the formula IV can for instance also be obtained by reacting a compound of the formula
S
H: Y r (VII), wherein R 6 has the meanings given for formula II, with a compound of the formula QX 1 wherein Q is an acidic group, preferably an inorganic acidic group, such as SO 2
X
1 and X, has the meanings given for formula II, in order to obtain a compound of the formula IV, wherein n 0 ist, and if desired further reacting the compound of the formula IV, wherein n is 0, with an oxidizing agent, such as hydrogenperoxid, in order to obtain a compound of the formula IV, wherein n is 1 or 2.
The compounds of the formula VII can for instance be obtained by reacting a compound of the formula VI with a compound of the formula R6X 2 wherein Re has the meaning as given for formula II and X 2 is a leaving group, preferably in the presence of a base.
The invention relates to all those embodiments of the process which are based on starting materials or intermediates obtainable from any stage of the process and in which all or some of the missing steps are carried out or in which a starting material is used or, in particular, formed under the reaction conditions in the form of a derivative or salt and/or its racemates or enantiomers.
The invention relates in particular to the processes described in Examples H1 to H8.
The Examples that follow more particularly describe the invention. They do not limit the invention. Temperatures are stated in degrees centigrade. Percentages represent "percent by weight', unless indicated otherwise.
Examples Example H1: 2-Benzylthio-5-chloromethyl-thiazole (Compound No. 1.9 in Table 1) 3.2 g of 2-benzylthio-5-methylene-4H-thiazoline are dissolved in 50 ml of dichloromethane, and 0.9 g of pulverulent sodium bicarbonate are added with stirring. The mixture is subsequently cooled in an ice bath, 1.92 g of sulfuryl chloride in 5 ml of dichloromethane are added dropwise, and stirring is then continued for a further 45 minutes. The reaction mixture is filtered, the filtrate is evaporated, and the residue is recrystallized from petroleum ether, yielding 1.4 g of the title compound in the form of crystals melting at 57 to 580.
Example H2: 3-(2-Benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5oxadiazine (Compound No. 2.9 in Table 2) 0.8 g of 2-benzylthio-5-chloromethyl-thiazole, 0.35 g of 3 methyl-4 nitroimino-perhydro- 1,3,5-oxadiazine and 0.8 g of pulverulent potassium carbonate are mixed in 40 ml of N,Ndimethylformamide, and the mixture is stirred at 600 for 2 hours. The reaction mixture is filtered, the filtrate is evaporated under reduced pressure, and the residue is digested in diethyl ether/isopropanol yielding 0.6 g of the title compound in the form of crystals melting at 140 to 145" (decomposition).
-11 Example H3: 3-(2-Chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine (Compound No. 11.1 in Table 11) 2 g of 3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine are dissolved in a mixture of 10 ml of 4N aqueous hydrochloric acid, 20 g of ice and 30 ml of dichloromethane, and 30 g of Javelle water are added dropwise with stirring to the solution. After stirring for a further 30 minutes, the organic phase is separated off, the aqueous phase is extracted repeatedly with a little dichloromethane, and the combined organic phases are subsequently dried with sodium sulphate and evaporated under reduced pressure. The oily residue is dissolved in tetrahydrofuran and precipitated with hexane, whereby the product deposits on the walls of the vessel as a sticky material. The solvent is decanted, the residue is redissolved in tetrahydrofuran, and the solution is slowly concentrated, yielding 0.84 g of the title compound in the form of a semi-crystalline resin. A sample of this resin is purified by chromatography [silica gel; dichloromethane/methanol yielding crystals melting at 132 to 135".
Example H4: 3-(2-Chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine (Compound No. 11.1 in Table 11) To a mixture of 300 g of aqueous hydrochloric acid and 150 g of chlorobenzene are added with stirring 183 g of 5-methyl-4-nitroimino-3-(2-phenylthiothiazol-5-ylmethyl)perhydro-1,3,5-oxadiazine within 5 minutes. 124 g of chlorine are then passed into the mixture at 20 to 25* over a period of 4 hours. After stirring for a further 2 hours, the excess of chlorine is removed by introduction of nitrogen, and the aqueous phase (containing the title compound in hydrochloride form) is separated off and adjusted to pH 5 with aqueous sodium hydroxide solution The crystalline precipitate is filtered off, washed with water and dried at 500 in vacuo, yielding 132 g of the title compound (purity: 97%) melting at 132 to 135°.
Example H5: 3-(2-Chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine (Compound No. 11.1 in Table 11) To a mixture of 300 g of aqueous hydrochloric acid and 150 g of chlorobenzene are added with stirring 186 g of 3-(2-cyclohexylthiothiazol-5-ylmethyl)-5-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine within 5 minutes. 124 g of chlorine are then passed into the mixture at 20 to 250 over a period of 4 hours. After stirring for a further 2 hours, the excess of chlorine is removed by introduction of nitrogen, and the aqueous phase (containing the -12title compound in hydrochloride form) is separated off and adjusted to pH 5 with aqueous sodium hydroxide solution The crystalline precipitate is filtered off, washed with water and dried at 500 in vacuo, yielding 135 g of the title compound (purity: 97%) melting at 132 to 135°.
Example H6: 3-(2-Chlorothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perydro-1,3,5-oxadiazine (Compound No. 11.1 in Table 11) To a mixture of 300 g of aqueous hydrochloric acid and 150 g of chlorobenzene are added with stirring 190 g of 3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine within 5 minutes. 124 g of chlorine are then passed into the mixture at 20 to 250 over a period of 4 hours. After stirring for a further 2 hours, the excess of chlorine is removed by introduction of nitrogen, and the aqueous phase (containing the title compound in hydrochloride form) is separated off and adjusted to pH 5 with aqueous sodium hydroxide solution The crystalline precipitate is filtered off, washed with water and dried at 500 in vacuo, yielding 120 g of the title compound (purity: 97%) melting at 132 to 135".
Example H7: 2-Benzylthio-5-methylene-4H-thiazoline (Compound No. 1.8 in Table la) A mixture of 6.5 g of 5-methylene-2-thioxo-thiazolidine, 17.3 g of pulverulent potassium carbonate, 9.4 g of benzyl bromide and 200 ml of acetonitrile is stirred for 1 hour at 65". The mixture is allowed to cool to room temperature and is then filtered, and the filtrate is evaporated to dryness in vacuo. The residue is purified by chromatography [silica gel; hexane/diethyl ether yielding 7.7 g of the title compound in the form of a colourless oil.
Example H8: Analogously to the procedures described in Examples H1 to H7, also the other compounds listed in Tables 1 to 13 can be prepared. The temperatures stated in the column 'Physical data" of these tables in each case denote the melting point of the respective compound; "decomp." means decomposition.
Table 1 (O)n
S
RNr Compound No. n X, R 6 Physical data 1.1 0 Cl CH 3 1.2 0 Cl CA, 1.3 0 CI n-C 3
H
7 1.4 0 Cl i-C, 2
H
7 0 CI n-C 4 Hq 1.6 0 Cl t-C 4 H-1 9 1.7 0 Cl CYClO-C 3 H-1 1.8 0 Cl CH 2 CrHs 57-580 (hydrochloride: 129-1 31 0) 1.9 0 Cl CH 2
C
6
H
4 -4-CH 3 1.10 0 Cl CH 2
C
6
H
4 -4-OCH 3 1.11 0 Cl CH 2
C
6
H
4 -4-CI 1.12 0 Cl CH 2 CsH 4 -4-N0 2 1 .13 0 Cl CH 2 -2-furyl 1 .14 0 Cl CH- 2 -2-thienyl 1.15 0 Cl C 6 1- 1.16 0 Cl C 6 H4-4-CH 3 1.17 0 Cl C 6
H
4 -4-OCH 3 1.18 0 Cl C 6 H-1 4 -4-CI 1.19 0 Cl C 6
H
4 -4-N0 2 1.20 0 Cl CH 2
CH=CH
2 1.21 0 Cl CH 2
C=-CH
1.22 0 Cl CH 2
CH=CHC
6
H
1.23 0 Cl CH 2
C-=CC
6 Hs 1.24 0 Cl SCH 3 -14- 1.25 0 CI SC 2 Hs 1.26 0 CI S-n-C 3
H
7 1.27 0 Cl S-i-C 3
H
7 1.28 0 CI S-n-C 4 Hq 1.29 0 CI S-t-C 4
H,
1.30 0 CI S-CYClo-C 3 Hs 1.31 0 CI SCH 2 CEHs 1.32 0 CI SCH 2
C
6
H
4 -4-CH 3 1.33 0 CI SCH 2
C
6
H
4 -4-OCH 3 1.34 0 CI SCH 2
C
6
H
4 -4-CI 1.35 0 CI SCH 2
C
6
H
4 -4-N0 2 1.36 0 CI SCH 2 -2-furyl 1.37 0 CI SCH 2 -2-thienyl 1.38 0 CI SC 6
H
1.39 0 CI SC 6
H
4 -4-0H 3 1.40 0 CI SC 6
H
4 -4-OCH 3 1.41 0 CI SC 6
H
4 -4-CI 1.42 0 CI SC 6
H
4 -4-N0 2 1.43 0 CI SCH 2
CH=CH
2 1.44 0 CI SCH 2
C=-CH
1.45 0 CI SCH 2 CH=CHCeHs 1.46 0 CI SCH 2 1.47 0 CI 1.48 1 CI CH 3 1.49 1 CI C 2 Hs 1.50 1 CI n-C 3
H
7 1.51 1 CI i-C 3
H
7 1.52 1 CI n-C 4
H
9 1.53 1 CI t-C 4
H
9 1.54 1 CI CYClO-C 3
H
1.55 1 CI CH 2 0 6
H
1.56 1 CI CH 2
C
6
H
4 -4-CH 3 1.57 1 CI CH 2
C
6
H
4 -4-OCH 3 1.58 1 CI CH 2
C
6
H
4 -4-CI 1.59 1 CI CH 2
C
6
H
4 -4-N0 2 1.60 1 CI CH 2 -2-furyl 1.61 1 CI CH 2 -2-thienyl 1.62 1 Cl CAH 1.63 1 Cl C 6
H
4 -4-CH 3 1.64 1 CI C 6
H
4 -4-OCH 3 1 .65 1 CI CrH 4 -4-CI 1.66 1 CI C 6
H
4 -4-N0 2 1.67 1 CI CH 2
CH=CH
2 1.68 1 CI CH 2
C=-CH
1.69 1 CI CH 2
CH=-CHC
6
H
1.70 1 CI CH 2
C-=CC
6
H
1.71 2 CI CH 3 1.72 2 CI C 2 1.73 2 CI n-C 3
H
7 1.74 2 CI i-C 3
H
7 1.75, 2 CI n-C 4 Hg 1.76 2 CI t-C 4
H
9 1.77 2 CI CYClO-C 3
H
1.78 2 CI CH 2
C
6 Hs 1.79 2 CI CH 2
C
6
H
4 -4-CH 3 1.80 2 CI CH 2
C
6
H
4 -4-OCH 3 1.81 2 CI CH 2
C
6
H
4 -4-CI 1.82 2 CI CH 2
C
6
H
4 -4-N0 2 1.83 2 CI CH 2 -2-furyl 1.84 2 CI CH 2 -2-thienyl 1.85 2 CI CAH 1.86 2 CI C 6
H
4 -4-CH 3 1.87 2 CI C 6
H
4 -4-OCH 3 16- 1.88 2 Cl C 6
H
4 -4-CI 1.89 2 CI C 6
H
4 4-N0 2 1.90 2 CI CH 2
CH=-CH
2 1.91 2 CI CH 2
C=-CH
1.92 2 CI CH 2 CH--CHC6Hs 1.93 2 CI CH 2
C=-CC
6 Hs 1.94 0 CI CH 2
SCH
3 1.95 0 CI CH 2
SC
2 Hs 1.96 0 CI CH 2 S-n-C 3
H
7 1.97 0 CI CH 2 S-i-C 3
H
7 1.98 0 CI CH 2 S-n-C 4
H
9 1.99 0 CI CH 2 S-t-C 4
H
9 1.100 0 CI CH 2 S-CYClO-C 3 Hs 1.101 0 CI CH 2
SCH
2
C
6
H
1.102 0 CI CH 2
SCH
2
C
6
H
4 -4-CH3 1.103 0 CI CH 2
SCH
2 CsH 4 -4-OCH3 1.104 0 CI CH 2
SCH
2
C
6
H
4 -4-CI 1.105 0 CI CH 2
SCH
2 CsH 4 -4-N0 2 1.106 0 CI CH 2
SCH
2 -2-turyl 1.107 0 CI CH 2
SCH
2 -2-thienyl 1.108 0 CI CH 2 SC6HS 1.109 0 CI CH 2
SC
6
H
4 -4-CH 3 1.110 0 CI CH 2
SC
6
H
4 -4-OCH 3 1.111 0 CI CH 2
SC
6
H
4 -4-CI 1.112 0 CI CH 2
SC
6
H
4 -4-N0 2 1.113 0 CI CH 2
SCH
2 CH=0CH 2 1.114 0 CI CH 2
SCH
2
C-=CH
1.115 0 CI CH 2
SCH
2
CH=CHC
6 Hs 1.116 0 CI CH 2
SCH
2
C-=CC
6 Hs 1.117 0 CI C H s S' >Nk 17- 1.118 0 Br CH 3 1.119 0 Br CAII 1.120 0 Br n-C 3
H
7 1.121 0 Br i-C 3
H
7 1.122 0 Br n-C 4 H9 1.123 0 Br t-C 4
H
9 1.124 0 Br CYClO-C 3
H
5 1.125 0 Br CH 2
C
6 Hs 1.126 0 Br CH 2
C
6
H
4 -4-CH 3 1.127 0 Br CH 2 CrH 4 -4-00H 3 1.128 0 Br CH 2
C
6
H
4 -4-CI 1.129 0 Br CH 2
COH
4 -4-N0 2 1.130 0 Br CH 2 -2-furyl 1.131 0 Br CH 2 -2-thienyl 1.132 0 Br CAH 99-1020 1.133 0 Br C 6
H
4 -4-CH 3 1.134 0 Br C6H4-4-OCH 3 1.135 0 Br C 6
H
4 -4-CI 1.136 0 Br C 6
H
4 -4-N0 2 1.137 0 Br CH 2
CH=CH
2 1.138 0 Br CH 2
C=-CH
1.139 0 Br CH 2
CH=CHC
6 H r 1.140 0 Br CH 2
C-=CC
6
H
1.141 0 Br SCH 3 1.142 0 Br SC 2
H
1.143 0 Br S-n-C 3
H
7 1.144 0 Br S-i-C 3
H
7 1.145 0 Br S-n-C 4 Hq 1.146 0 Br S-t-0 4 Hq 1.147 0 Br S-CYClO-C 3
H
1.148 0 Br SCH 2 C6Hs 1.149 0 Br SCH 2
C
6
H
4 -4-CH 3 1.150 0 Br SCH 2
C
6
H
4 -4-OCH 3 -18- 1.151 0 Br SCH 2
C
6
H
4 -4-CI 1.152 0 Br SCH 2
C
6
H
4 -4-N0 2 1.153 0 Br SCH 2 -2-furyI 1.154 0 Br SCHr-2-thienyl 1.155 0 Br SC 6
H
5 1.156 0 Br S0 6
H
4 -4-0H 3 1.157 0 Br SC 6
H
4 -4-OCH 3 1.158 0 Br SC 6
H
4 -4-CI 1.159 0 Br SC;H, 4 -4-N0 2 1.160 0 Br SCH 2 CH=0H 2 1.161 0 Br SCH 2
CE-CH
1.162 0 Br SCH 2 1.163 0 Br SCH 2
C=-CC
6
H
1.164 0 Br 1.165 1 Br OH 3 1.166 1 Br CAH 1.167 1 Br n-C 3
H
7 1.168 1 Br i-C 3 H7 1.169. 1 Br n-C 4
H
9 1.170 1 Br t-C 4
H
9 1.171 1 Br CYClO-0 3
H
1.172 1 Br CH 2 CrHs 1.173 1 Br CH 2
C
6 H4-4-CH 3 1.174 1 Br CH 2
C
6
H
4 -4-OCH 3 1.175 1 Br 0H 2
C
6
H
4 -4-CI 1.176 1 Br CH 2
C
6
H
4 -4-N0 2 1.177 1 Br CH 2 -2-furyl 1.178 1 Br 0H 2 -2-thienyl 1.179 1 Br C 6
H
1.180 1 Br 0 6
H
4 -4-CH 3 -19- 1.181 1 Br C 6
H
4 -4-OCH 3 1.182 1 Br C6H 4 -4-CI 1.183 1 Br 0 6
H
4 -4-N0 2 1.184 1 Br CH 2
CH=CH
2 1.185 1 Br CH 2
C-=CH
1.186 1 Br CH 2
CH=CHC
6
H
1.187 1 Br CH 2
C-=CC
6 1.188 2 Br CH 3 1.189 2 Br CAH 1.190 2 Br n-C3H 7 1.191 2 Br i-C 3
H
7 1.192 2 Br n-C 4 Hq 1.193 2 Br t-C 4
H
9 1.194 2 Br CYClO-C 3
H
1.195 2 Br CH 2
C
6 1.196 2 Br CH 2
C
6
H
4 -4-CH 3 1.197 2 Br CH 2
C
6
I-
4 -4-OCH 3 1.198 2 Br CH 2
C
6
H
4 -4-CI 1.199 2 Br CH 2
C
6
H
4 -4-N0 2 1.200 2 Br CH 2 -2-furyl 1.201 2 Br CH 2 -2-thienyl 1.202 2 Br C 6
H
1.203 2 Br C 6
H
4 -4-0H 3 1.204 2 Br C 6
H
4 -4-OCH 3 1.205 2 Br C 6
H
4 -4-CI 1.206 2 Br C 6 H4-4-N0 2 1.207 2 Br CH 2 CI-=0H 2 1.208 2 Br CH 2
C=-CH
1.209 2 Br CH 2
CH=CHC
6
H
1.210 2 Br CH 2
C-=OC
6
H
1.211 0 Br CH 2
SCH
3 1.212 0 Br CH 2
SC
2
H
1.213 0 Br CH 2 S-n-C 3
H
7 20 1.214 0 Br CH 2 S-i-C 3 H-1 1.215 0 Br CH 2 S-n-C 4 H9 1.216 0 Br CH 2 S-t-C 4
H
9 1.217 0 Br CH 2 S-CYClO-C 3
H
1.218 0 Br CH 2
SCH
2
CGH
1.219 0 Br CH 2
SCH
2
C
6
H
4 -4-CH 3 1.220 0 Br CH 2
SCH
2 C6H 4 -4-OCH3 1.221 0 Br CH 2
SCH
2 CrH4-4-CI 1.222 0 Br CH 2
SCH
2
C
6
H
4 -4-N0 2 1.223 0 Br CH 2
SCH
2 -2-furyl 1.224 0 Br CH 2
SCH
2 -2-thienyl 1.225 0 Br CH 2 SCrH 1.226 0 Br CH 2 SC6H 4 -4-CH 3 1.227 0 Br CH 2 SCrH4-4-OCH 3 1.228 0 Br CH 2 SCrH 4 -4-CI 1.229 0 Br CH 2
SC
6
H
4 -4-N0 2 1.230 0 Br CH 2
SCH
2 CH=0CH 2 1.231 0 Br CH 2
SCH
2
C-=OH
1.232 0 Br CH 2
SCH
2
CH=-CHC
6 Hs 1.233 0 Br CH 2
SCH
2
C-=CC
6
H
1.234 0 Br CH 2 N O
NQJ
1.235 0 Ci CH 2 C0%--'pH 1.236 0 clCI yIO-( 6 H 1 1 1.237 0 CI CH 2
-CH
2
-CH
2
-CH
2
-CH
2
-SH
1.238 0 CI CH 2
CO
2 Na 1.239 0 Br CH 2 00 2
C
2 Hs 1.240 0 Br CYClO-C6H~l 1.241 0 B r CH 2
-CH
2
-CH
2
-CH
2
-CH
2
-SH
1.242 0 B r CH 2 00 2 Na 21- 1.243 0 CI l N.NO 2 0 CIj 1.244 0 CI N O
N
1.245 0 CI NCN CN$ N
NCH
1.247 0 CI N N 1.248 0 CI 1.249 12490 CI 22 1.250 0 CI OH 2 N CN D/H'Nk -C H 1.252 0 CI CH 2 N--N02 N N. CH 3
NN
H
3
C
1.253 0 CI H N-N2 N CH 3 H 3 c 1.254 0 CI H N CN N~
N
4
I
I
NN
23 1.256 0 CI CH 2 N "N02 S N 1 1.257 0 CI
N..CN
N:N
1.258 0 CI CH 2
N.C
N:
1.259 0 CI N "N02 N J0 1.261 0 clC H NC 1.262 0 CI CK 1.263 12630 CI 24 1.264 1.265 o ci o ci o ci o ci
CH
2 N'-NO2 1.266 1.267 1.268 0 Ci
OH
2
N-
1.269.
0 Br 1.270 1700 Br O cH
N
HO NN
~ON-NS
Nfl NO N HO JSl 0 LLZL J8 0 9LZ*L
.N
HO
J9 0 Jg3 0 J13 0 isg 0 NH
N
NO
NS
JS 0 L~I LLZ* L Sz -26 1.278 1.279 o Br OH 2 NO N 2 r/N lNCH 3
NN
H
3
C
0 Br N Ojl H 3
NN
H
3 0 1.28nl 1.28 1 o Br CH 2 0 Br N- NO 2 1.282 0 Br
,NO
2 1.2P3 0 Br 1.284 0 Br CH 2 N O N~r -27- 1.285 0 Br 1.286 0 Br 1.287 0 Br 1.288 0 Br
OH
2 1.289 0 Br 1.290 0 Br 1.291 0 Br 1.292 1920 Br -28- 1.293 1.294 0 Br 0 Br TabIl la Compound No. R 6 Physical data 1.1a 1 .2a 1 .3a 1.4a 1.6a 1.7a 1 .8a 1 .9a 1.10Oa 1.1lla 1.12a 1.1 3a 1.14a 1.15a 1.1 6a 1.17a
OH
3
C
2 1n-C 3
H
7 i-C 3
H-
7 n-C 4
H-
9 t-0 4
H-
9 CYClo-C 3
H
CH
2
C
8
H
CH
2
C
6
H
4 -4-CH 3
CH
2
C
6
H
4 -4-OCH 3
CHAC
6
H
4 -4-CI
CHACH
4 -4-N0 2
CH
2 -2-furyl
CH
2 -2-thienyl
C
6 1- C61H 4 -4-CH 3
C
6
H-
4 -4-OCH- 3 oil -29 1.18Ba 1.19a 1 .20a 1.21 a 1 .22a 1 .23a 1.24a 1.25a 1.26a 1.27a 1.28a 1.29a 1.30a 1.31 a 1.32a 1.33a 1.34a 1.35a 1.36a 1.37a 1.38a 1.39a 1.40a 1.41 a 1.42a 1.43a 1.44a 1.45a 1.46a 1.47a
C
6
H
4 -4-CI
C
6
H
4 -4-N0 2
CH
2
CH=CH
2
CH
2
C-=CH
CH
2
CH=CHC
6 Hs
CH
2 C-=Cc 6 Hs
SCH
3
SC
2
H
S-n-C 3
H
7 S-i-C 3
H
7 S-n-0 4
H
9 S-t-C 4
H
9
S-CYCIO-C
3 Hs,
SCH
2
C
6
H
SCH
2
C
6
H
4 -4-CH 3
SCH
2
C
8
H
4 -4-OCH 3
SCH
2
C
6
H
4 -4-CI
SCH
2 C6H 4 -4-N0 2
SCH
2 -2-furyl
SCH
2 -2-thienyl
SC
6
H
SCH4-4-CH 3
SC
6
H
4 -4-OCH 3
SC
6 H4-4-CI
SC
6
H
4 -4-N0 2
SCH
2
CH=CH
2
SCH
2
C-=CH
SCH
2 CH=0H0 6 Hs
SCH
2
CE-CC
6 Hs
D?
2 1.5924 N N02 1 .48a CH 2
SCH
3 1 .49a CH 2
SC
2
H
1 .50a CH 2 S-n-C 3
H
7 1.51 a CH 2 S-i-C 3
H
7 1 .52a CH 2 S-n-C 4 H9 1 .53a CH 2 S-t-0 4
H
9 1 .54a CH 2 S-CYClO-C 3 Hs 1.55a CH 2
SCH
2
C
5 Hs 1.56a CH 2
SCH
2
C
6
H
4 -4-CH 3 1 .57a CH 2
SCH
2
C
6
H
4 -4-OCH 3 1.58a CH 2
SCH
2 CsH 4 -4-CI 1 .59a CH 2
SCH
2
C
6
H
4 -4-N0 2 1 .60a CH 2 SCHr-2-furyl 1 .61 a CH 2
SCH
2 -2-thienyt 1.62a CH 2
SC
6 Hs 1 .63a CH 2 SCsH 4 -4-0H 3 1 .64a CH 2
SC
6
H
4 -4-OCH 3 1 .65a CH 2
SC
6
H
4 -4-Cl 1 .66a CH 2
SC
6
H
4 -4-N0 2 1 .67a CH 2
SCH
2
CH=CH
2 1 .68a CH 2
SCH
2
C-=OH
1 .69a CH 2
SCH
2
CH=CHC
6
H
1 .70a CH 2
SCH
2 C-CCeH 1.71 a CH2 NNO
NJ
1.72a CH 2
CO
2
C
2
H
1 .73a CYClo-C 6
H
11 1 .74a CH 2
-CH
2 -0H 2
-CH
2
-CH
2
-SH
1 .75a CH 2 00 2 Na -31 1 .76a sN NO2 N N N-CH3 (0 1 .77a sN -NO 1.78a N CN N)NNJ\ NCH: 1.79a NC
CH
2 N 0 1 .80a S-~sN-N02 N N -N.CH 1.81la fH~ 1.82a 32 1 .83a OH 2 N- CN N y.CH 3 1.84a sN'-N02 N
N
I
HOC
1.85a CH2C 2
NN
H
3
C
1.86a OH 2 s C
NN
I
H
3 0 1.88a 33- 1.89a 1.90a 1.91 a 1.92a 1.93a
CH
2 1.94a 1.95a 1.96a -34- 1 .97a
OH
2 N'-N02 1.98a 1.99a 1.100a 1.101a CH2 Nll Table 2 Compound No.
2.1 2.2 2.3 Y R
NO
2
OH
3
NO
2
C
2 Hs N0 2 n-C 3 Physical data 135-1370
H
7 67-720 35 2.4 0 NO 2 i-C 3 H-i 0 NO 2 n-0 4
H
9 2.6 0 NO 2 t-0 4
H
9 2.7 0 NO 2 CYClO-0 3
H
2.8 0 NO 2 CYCtO-0 6 H I 1 109-1100 2.9 0 NO 2
CH
2
C
6
H
5 140-1450 (decomp.) 2.10 0 NO 2
'CH
2 0 6
H
4 -4-CH 3 2.11 0 NO 2
CH
2
C
6
H
4 -4-OCH 3 2.12 0 NO 2
CH
2 CeH 4 -4-CI 2.13 0 NO 2 0H 2 CeH 4 -4-N0 2 2.14 0 NO 2
CH
2 -2-furyt 2.15 0 NO 2
CH
2 -2-thienyl 2.16 0 NO 2 CsHs 1470 2.17 0 NO 2
C
5
H
4 -4-0H 3 160.1620 2.18 0 NO 2
C
6
H
4 -4-OCH 3 2.19 0 NO 2 0 6
H
4 -4-CI 2.20 0 NO 2
C
6
H
4 -4-N0 2 2.21 0 ON CH 2
SCH
2 C,-cc 6
HS
2.22 0 NO 2
CH
2 CH=0-H 2 2.23 0 NO 2
CH
2
C-=OH
2.24 0 NO 2
CH
2
CH=O-HC
6
H
2.25 0 NO 2
CH
2
C=-CC
6 Hs 2.26 0 NO 2 0H 2
-CH
2
-CH
2
-CH
2
-CH
2 -SH 57-600 2.27 0 NO 2
CH
2 00 2
C
2
H
2.28 0 NO 2
CH
2 C0 2 Na 130.1380 (decomp.) 2.29 0 NO 2
SCH
3 2.30 0 NO 2
SC
2
H
2.31 0 NO 2 S-n-0 3
H
7 2.32 0 NO 2 S-i-C 3
H
7 2.33 0 NO 2 S-n-C 4 Hq 2.34 0 NO 2 S-t-0 4 Hq 36 2.35 0 NO 2 S-CYClO-C 3 Hs 2.36 0 NO 2
SCH
2
C
6 2.37 0 NO 2
SCH
2
C
6
H
4 -4-CH 3 2.38 0 NO 2
SCH
2
C
6
H
4 -4-00H3 2.39 0 NO 2
SCH
2 CeHs4-CI 2.40 0 N0 2 SCHACH4-4-N0 2 2.41 0 NO 2 SCHr2-fUryl 2.42 0 NO 2 SCH2-2-thienyl 2.43 0 NO 2
SC
6
H
2.44 0 NO 2 SCsH 4 -4-0H 3 2.45 0 NO 2 SCsH 4 -4-00H 3 2.46 0 NO 2
SC
6
H
4 -4-OI 2.47 0 NO 2
SC
6
H
4 -4-NO 2 2.48 0 NO 2
SCH
2
CH=CH
2 2.49 0 NO 2
SCH
2
C=-OH
2.50 0 NO 2
SCH
2 2.51 0 N0 2
SCH
2
C-=CCGH
2.52 0 NO 2 NN02 2.53 1 NO 2
CH
3 2.54 1 NO 2
C
2
H
2.55 1 NO 2 n-C 3
H
7 2.56 1 NO 2 i-C 3
H
7 2.57 1 NO 2 n-C4H 9 2.58 1 NO 2 t-C 4
H
9 2.59 1 NO 2
CYCIO-C
3
H
2.60 1 NO 2
CH
2
C
6 H5 170-1800 2.61 1 NO 2
CH
2
C
6
H
4 -4-CH 3 2.62 1 NO 2
CH
2 C6H 4 -4-OCH 3 2.63 1 NO 2
CH
2
C
6
H
4 -4-CI 2.64 1 NO 2
CH
2
C
6
H
4 -4-N0 2 -37.
2.65 1 NO 2
CH
2 -2-furyl 2.66 1 NO 2
CH
2 -2-thienyl 2.67 1 NO 2
C
6
H
2.68 1 NO 2 CrH 4 4CH 3 2.69 1 NO 2
C
6
H
4 -4-OCH 3 2.70 1 NO 2
C
6
H
4 -4-CI 2.71 1 NO 2
C
6
H
4 -4-N0 2 2.72 1 NO 2
CH
2
CH=CH
2 2.73 1 NO 2
CH
2 Ca-CH 2.74 1 NO 2
CH
2
CH=CHC
6 Hs 2.75 1 NO 2
CH
2 C=-CC6Hs 2.76 2 NO 2
OH
3 1570 2.77 2 NO 2
C
2
H
2.78 2 NO 2 n-C 3
H
7 resin 2.79 2 NO 2 i-0 3
H
7 2.80 2 NO 2 n-C 4 H9 2.81 2 NO 2 t-C 4 H9 2.82 2 NO 2 CYClO-C 3
H
2.83 2 NO 2
CH
2 0 6 Hs 160-1750 2.84 2 NO 2
CH
2
C
6
H
4 -4-CH 3 2.85. 2 NO 2
CH
2
C
6 H4-4-OCH 3 2.86 2 NO 2
CH
2
C
6
H
4 -4-CI 2.87 2 NO 2
CH
2 0 6
H
4 -4-N0 2 2.88 2 NO 2
CH
2 -2-furyl 2.89 2 NO 2
CH
2 -2-thienyl 2.90 2 NO 2 CAH 2100 2.91 2 NO 2
C
6
H
4 4-CH 3 2.92 2 NO 2
C
6
H
4 -4-OCH 3 2.93 2 NO 2
C
6
H
4 -4-Ct 2.94 2 NO 2
C
6
H
4 -4-N0 2 2.95 2 NO 2
CH
2 CH=0H 2 2.96 2 NO 2
CH
2
CEOCH
2.97 2 NO 2
CH
2 CH=OCHCsHs 38 2.98 2 NO 2
CH
2
C=-OC
6 Hs 2.99 0 NO 2
CH
2
SOH
3 2.100 0 NO 2
CH
2 S0 2 Hs 2.101 0 NO 2
CH
2 S-n-0 3
H
7 2.102 0 NO 2
CH
2
S--H
7 2.103 0 NO 2
OH
2 S-n-0 4
H,
2.104 0 NO 2
CH
2 S-t-0 4
H
9 2.105 0 NO 2
CH
2 S-CYClO-0 3
HF
2.106 0 NO 2
OH
2
SCH
2 O.Hs 2.107 0 NO 2
OH
2
SCH
2
O
6
H
4 -4-CH 3 2.108 0 NO 2
CH
2
SCH
2 CeH4-4-OCH 3 2.109 0 NO 2
OH
2
SCH
2
C
6
H
4 -4-Ot 2.110 0 NO 2
CH
2
SCH
2
O
6
H
4 -4-N0 2 2.111 0 NO 2
OH
2
SCH
2 -2-furyt 2.112 0 NO 2
CH
2
SCH
2 -2-thienyl 2.113 0 NO 2
CH
2 2.114 0 NO 2
CH
2
SC
6
H
4 -4-CH 3 2.115 0 NO 2
CH
2
SC
8
H
4 -4-OCH 3 2.116 0 NO 2
OH
2 SCsH 4 -4-CI 2.117 0 NO 2
CH
2
SC
6
H
4 -4-N0 2 2.118 0 NO 2
CH
2
SCH
2 CH=0H 2 2.119 0 NO 2
CH
2
SCH
2
C-=OH
2.120 0 NO 2
CH
2
SCH
2
CH=OCHC
5
H
2.121 0 NO 2
CH
2
SCH
2
C-=CC
6
H
2.122 0 NO 2 0' 2.123 0 ON CH 3 2.124 0 ON CAH 2.125 0 ON n-0 3
H
7 2.126 0 ON i-C 3
H
7 2.127 0 ON n-0 4
H
9 -39 2.128 0 ON t-C 4 H9 2.129 0 ON CYCIO-C 3 Hs 2.130 0 ON 0H 2
C
6 Hs 2.131 0 ON CH 2 0 8
H
4 -4-OH3 2.132 0 ON 0H 2 CrH 4 -4-00H 3 2.133 0 ON CH 2 0 6
H
4 -4-Oi 2.134 0 ON 0H 2
C
6
H
4 -4-N0 2 2.135 0 ON 0H 2 -2-furyl 2.136 0 ON OHr2-thienl 2.137 0 ON 0 6
H
2.138 0 ON 0 6
H
4 -4-CH 3 2.139 0 ON 0 6
H
4 -4-OCH 3 2.140 0 ON O 6
H
4 -4-OI 2.141 0 ON 0 6
H
4 -4-N0 2 2.142 0 ON OH 2 OH=0CH 2 2.143 0 ON CH 2
O-=OH
2.144 0 ON CH 2
CH=-CHC
6
H
2.145 0 ON CH 2
C-=CC
6 Hs 2.146 0 ON SOH 3 2.147 0 ON 50 2 Hs 2.148 0 ON S-n-0 3
H
7 2.149 0 ON S-i-0 3
H
7 2.150 0 ON S-n-C 4 Hq 2.151 0 ON S-t-0 4
H.
2.152 0 ON S-CYClO-0 3
H
2.153 0 ON SOH 2
C
6 Hs 2.154 0 ON S0H 2 0 6
H
4 -4-0H 3 2.155 0 ON S0H 2 0 6
H
4 -4-00H 3 2.156 0 ON S0H 2 0 6
H
4 -4-OI 2.157 0 ON S0H 2 0 6
H
4 -4-N0 2 2.158 0 ON SOH22-fryI 2.159 0 ON SOH 2 -2-thienyl 2.160 0 ON SC 6
H
2.161 0 ON S0 6
H
4 -4-0H 3 2.162 0 ON S0 6
H
4 -4-00H 3 2.163 0 ON S0 0
H
4 -4-CI 2.164 0 ON S0 6
H
4 -4-N0 2 2.165 0 ON SCH 2 CH=0CH 2 2.166 0 ON SCH 2 OmCH 2.167 0 ON SCH 2 CH=0CH0 6 Hs 2.168 0 ON SCH 2
O-=CC
6 Hs 2.169 0 ON 2.170 1 ON OH 3 2.171 1 ON C 2 Hs 2.172 1 ON n-0 3
H
7 2.173 1 ON i-CH 7 2.174 1 CN n-C 4 H9 2.175 1 ON t-C 4
H
9 2.176 1 ON CYClo-C 3
H
2.177 1 ON 0H 2 0 6 Hs 2.178 1 ON 0H 2 0 6
H
4 -4-0H 3 2.17 9 1 ON 0H 2 0 6
H
4 -4-00H 3 2.180 1 ON CH 2 CoH 4 -4-CI 2.181 1 ON OH 2 OsH-4-N0 2 2.182 1 ON 0H 2 -2-furyl 2.183 1 ON 0H 2 -2-thienyl 2.184 1 ON 0 6
H
2.185 1 ON C 6
H
4 -4-0H 3 2.186 1 ON 0 6
H
4 -4-00H 3 2.187 1 ON 0 6
H
4 -4-OI 2.188 1 ON 0 6
H
4 -4-N0 2 2.189 1 ON OH 2 OH=0CH 2 2.190 1 ON CH 2
O-=OH
-41 2.191 1 ON CH 2 CH=0H0 6
H
2.192 1 ON OH 2 O=-CCrHs 2.193 2 ON OH 3 2.194 2 ON C 2 Hs 2.195 2 ON n-0 3
H
7 2.196 2 CN i-0 3
H
7 2.197 2 ON n-C 4
H
9 2.198 2 ON t-0 4
H
9 2.199 2 ON CYclO-C 3
H
2.200 2 ON CHA0Hs 2.201 2 ON CH 2
C
6
H
4 -4-CH 3 2.202 2 ON 0HA0H 4 -4-00H 3 2.203 2 ON 0H 2 0 6
H
4 -4-OI 2.204 2 ON 0H 2 0 6
H
4 -4-N0 2 2.205 2 ON OH 2 -2-furyl 2.206 2 ON 0H 2 -2-thienyl 2.207 2 CN C 6 Hs 2.208 2 ON 0 6
H
4 -4-0H 3 2.209 2 ON 0 8
H
4 -4-00H 3 2.210 2 ON 0 6
H
4 -4-OI 2.211 2 CN 0 6
H
4 -4-N0 2 2.212 2 ON OH 2 OH=0H 2 2.213 2 ON CH 2
O-=OH
2.214 2 ON OH 2 OH=0H0 6
H
2.215 2 ON OH 2
O--OO
6
H
2.216 0 ON OH 2
SOH
3 2.217 0 ON 0H 2 S0 2
H
2.218 0 ON OH 2 S-n-0 3
H
7 2.219 0 ON OH 2 S-i-0 3
H
7 2.220 0 ON OH 2 S-n-0 4
H
9 2.22 1 0 ON 0H 2 S-tO 4 Hg 2.222 0 ON OH 2 S-CYClO-0 3
H
2.223 0 ON CH 2
SCH
2
C
6
H
-42- 2.224 0 CN CH 2
SCH
2
O
6
H
4 -4-CH 3 2.225 0 CN CH 2
SCH
2
C
6
H
4 -4-OCH 3 2.226 0 ON CH 2
SCH
2
C
6
H
4 -4-Ol 2.227 0 ON OH 2
SCH
2 C6I- 4 -4-N02 2.228 0 ON OH 2 SCHr2furyI 2.229 0 ON OH 2 SCHr2-thienyI 2.230 0 ON OH 2
SO
6 Hs 2.23 1 0 ON 0H 2 S0 8
H
4 -4-CH 3 2.232 0 ON 0H 2 S0 6
H
4 -4-00H 3 2.233 0 ON 0H 2 S0 6
H
4 -4-Ol 2.234 0 ON 0H 2 S0 6
H
4 -4-N0 2 2.235 0 ON OH 2
SOH
2 OH=0CH 2 2.236 0 CN CH- 2
SCH
2
O=-OH
2.237 0 ON OH 2
SOH
2 OH=OHC6H 2.238 0 ON hlC Table 3 (O)n N
QN
Compound No. n Y R6 Physical data 3.1 0 NO 2
OH
3 3.2 0 NO 2
C
2 1- 3.3 0 NO 2 n-0 3
H-
7 3.4 0 NO 2 i-0 3
H-
7 0 NO 2 n-0 4
H-
9 3.6 0 NO 2 t-0 4
H-
9 -43- 3.7 0 NO 2 CYClO-C 3 Hs 3.8 0 NO 2
CH
2
C
6
H
3.9 0 NO 2
CH
2
C.H
4 -4-CH 3 3.10 0 NO 2
CH
2
CH
4 -4-OCH3 3.11 0 NO 2
CH
2 CsH 4 -4-CI 3.12 0 NO 2 CHACH.-4-N0 2 3.13 0 NO 2
CH
2 -2-furyl 3.14 0 NO 2
CH
2 -2-thienyl 3.15 0 NO 2
CAH
3.16 0 NO 2
C
6
H
4 -4-CH3 3.17 0 NO 2
C
6
H
4 -4-OCH 3 3.18 0 NO 2
COH
4 -4-Cl 3.19 0 NO 2 0 6
H-
4 -4-N0 2 3.20 0 NO 2
CH
2
CH=CH
2 3.21 0 NO 2
CH
2
CE-CH
3.22 0 NO 2
CH
2 3.23 0 NO 2
CH
2
C-=CC
6
H
3.24 0 NO 2
SCH
3 3.25 0 NO 2
SC
2 Hs 3.26 0 NO 2 S-n-C 3
H
7 3.27 0 NO 2 S-i-C 3
H
7 3.28 0 NO 2 S-n-C 4 H9 3.29 0 NO 2 S-t-C 4 Hq 3.30 0 NO 2 S-CYClO-C 3 Hs 3.31 0 NO 2
SCH
2 C6Hs 3.32 0 NO 2
SCH
2
C
6
H
4 -4-CH 3 3.33 0 NO 2
SCH
2
C
6
H
4 -4-OCH 3 3.34 0 NO 2
SCH
2
C
6
H
4 -4-CI 3.35 0 NO 2
SCH
2
C
6
H
4 -4-N0 2 3.36 0 NO 2
SCH
2 -2-furyl 3.37 0 NO 2
SCH
2 -2-thienyl 3.38 0 NO 2
SC
6
H
3.39 0 NO 2
SC
6
H
4 -4-0H 3 -44- 3.40 0 NO 2 SCeH 4 -4-00H 3 3.41 0 NO 2 SCeH 4 -4-CI 3.42 0 NO 2
SC
6
H
4 -4-N0 2 3.43 0 NO 2
SCH
2 CH=0CH 2 3.44 0 NO 2
SCH
2
C=-CH
3.45 0 NO 2
SCH
2
CH--OHC
6 3.46 0 NO 2
SCH
2
C=-CC
6
H
3.47 0 NO 2 r
N
3.48 1 NO 2
OH
3 3.49 1 NO 2
CAH
3.50 1 NO 2 n-C 3
H
7 3.51 1 NO 2 i-C 3
H
7 3.52 1 NO 2 n-0 4
H
9 3.53 1 NO 2 t-C 4 Hq 3.54 1 NO 2 CYClO-C 3
H
3.55 1 NO 2
CHACH
3.56 1 NO 2
CH
2 CeH 4 -4-CH 3 3.57 1 NO 2
CH
2 CeH 4 -4-OCH 3 3.58 1 NO 2
CH
2
C
6
H
4 -4-CI 3.59 1 NO 2
CHACH
4 -4-N0 2 3.60 1 NO 2
CH
2 -2-furyl 3.61 1 NO 2
CH
2 -2-thienyt 3.62 1 NO 2
C
6 sH 3.63 1 NO 2
C
6
H,
4 -4-CH 3 3.64 1 NO 2 C6H 4 -4-OCH 3 3.65 1 NO 2
C
6
H
4 -4-CI 3.66 1 NO 2 CsH 4 -4-N0 2 3.67 1 NO 2
CH
2
CH=CH
2 3.68 1 NO 2
CH
2
CE=CH
3.69 1 NO 2
CH
2
CH=CHC
6
H
3.70 1 NO 2
CH
2
C=-CC.H
3.71 2 NO 2
CH
3 3.72 2 NO 2
C
2
H
3.73 2 NO 2 n-C 3
H
7 3.74 2 NO 2 i-C 3
H
7 3.75 2 NO 2 n-C 4 H9 3.76 2 NO 2 t-C 4
H
9 3.77 2 NO 2 CYClO-C 3
H
3.78 2 NO 2
CH
2
C
6 Hs 3.79 2 NO 2
CH
2
CBH
4 -4-CH 3 3.80 2 NO 2
CH
2
C
6
H
4 -4-OCH 3 3.81 2 NO 2
CH
2
C
6
H
4 -4-CI 3.82 2 NO 2
CH
2
C
6
H
4 -4-N0 2 3.83 2 NO 2
CH
2 -2-turyt 3.84 2 NO 2
CH
2 -2-thienyt 3.85 2 NO 2
CAH
3.86 2 NO 2
C
6
H
4 -4-CH 3 3.87 2 NO 2
C.H
4 -4-OCH 3 3.88 2 NO 2
COH
4 -4-Cl 3.89 2 NO 2
C
6
H
4 -4-N0 2 3.90 2 NO 2
CH
2 CH=0CH 2 3.91 2 NO 2
CH
2
C=-CH
3.92 2 NO 2
CH
2 CH=-CHCsHs 3.93 2 NO 2
CH
2 C-=CC6Hs 3.94 0 NO 2
CH
2
SCH
3 3.95 0 NO 2
CH
2
SC
2
H
3.96 0 NO 2
CH
2 S-n-0 3
H
7 3.97 0 NO 2
CH
2 S-i-0 3
H
7 3.98 0 NO 2
CH
2 S-n-C 4 H9 3.99 0 NO 2
CH
2 S-t-0 4
H
9 3.100 0 NO 2
CH
2 S-CYClO-C 3
H
3.101 0 NO 2
CH
2
SCH
2 C6HS 3.102 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CH 3 46- 3.103 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-OCH3 3.104 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-Cl 3.105 0 NO 2
CH
2
SCH
2 C6H-4-N02 3.106 0 NO 2
CH
2
SCH
2 -2-furyl 3.107 0 NO 2
OH
2 SCHr2-thienyl 3.108 0 NO 2
CH
2
SO
6 Hs 3.109 0 NO 2
CH
2
SO
6
H
4 -4-CH 3 3.110 0 NO 2
CH
2
SC
6
H
4 -4-00H 3 3.111 0 NO 2
CH
2
SCOH
4 -4-CI 3.112 0 NO 2
CH
2
SC
6
H
4 -4-N02 3.113 0 NO 2
OH
2
SCH
2 CH=0CH 2 3.114 0 NO 2
CH
2
SCH
2 CeOCH 3.115 0 NO 2
OH
2
SCH
2 CH=0CH0 6 Hs 3.116 0 NO 2
CH
2
SCH
2
C=-OC
6
H$
3.117 0 NO 2
CH
2 3.118 0 CN OH 3 3.119 0 CN C 2 Hs 3.120 0 CN n-C 3
H
7 3.121 0 CN i-0 3
H
7 3.122 0 ON n-C 4
H
9 3.123 0 CN t-0 4
H
9 3.124 0 ON CYClO-C 3
H
3.125 0 ON CH 2 0 6
H
3.126 0 ON 0H 2
C
6 H4-4-CH 3 3.127 0 ON 0H 2 0 6
H
4 -4-OCH3 3.128 0 ON CH 2 0 6
H
4 -4-OI 3.129 0 ON OH 2
COH
4 -4-N0 2 3.130 0 CN CH 2 -2-furyl 3.131 0 ON CH 2 -2-thienyl 3.132 0 ON 0 6
H
-47 3.133 0 ON 0 6
H
4 -4-CH 3 3.134 0 ON C 6
H
4 -4-OCH 3 3.135 0 ON 0 6
H
4 -4-CI 3.136 0 ON 0 6
H
4 -4-N0 2 3.137 0 ON OH 2 CH=0CH 2 3.138 0 ON CH 2
O-=CH
3.139 0 ON OH 2
CH--CHC
6 Hs 3.140 0 CN CH 2 C-=CCrHs 3.141 0 ON SOH 3 3.142 0 ON S0 2
H
3.143 0 ON S-n-0 3
H
7 3.144 0 ON S-i-CH 7 3.145 0 ON S-n-0 4 Hq 3.146 0 ON S-t-0 4 Hq 3.147 0 ON S-CYClO-C 3 Hs 3.148 0 ON S0H 2 0 6 Hs 3.149 0 CN SCH 2
C
6
H
4 -4-CH 3 3.150 0 ON S0H 2 0 6
H
4 -4-00H 3 3.151 0 ON S0H 2 0 6
H
4 -4-OI 3.152 0 ON S0H 2 0 6
H
4 -4-N0 2 3.153 0 ON SOH 2 -2-furyl 3.15 4 0 ON SOH 2 -2-thienyl 3.155 0 ON S0 6 Hs 3.156 0 ON SO 6
H
4 -4-0H 3 3.157 0 ON S0 6
H
4 -4-00H 3 3.158 0 ON S0 6
H
4 -4-OI 3.159 0 ON S0 6
H
4 -4-N0 2 3.160 0 ON SOH 2 OH=0CH 2 3.161 0 ON SCH 2
O-=CH
3.162 0 ON SOH 2
OH=OHC
6
H
3.163 0 ON SCH 2
C-=CC
6
H
48 3.164 0 CN -O sN C 3.165 1 CN OH 3 3.166 1 ON 0 2 Hs 3.167 1 ON n-0 3
H
7 3.168 1 CN i-C 3
H
7 3.169 1 ON n-0 4
H
9 3.170 1 ON t-C 4
H
9 3.171 1 ON cydlo-0 3 Hs 3.172 1 ON OH 2
C
6 3.173 1 ON 0H 2 0 6
H
4 -4-0H 3 3.174 1 ON 0H 2 0 6
H
4 -4-00H 3 3.175 1 ON 0H 2 0 6
H
4 -4-CI 3.176 1 ON 0H 2 0 6
H
4 -4-N0 2 3.177 1 ON CH 2 -2-furyl 3.178 1 ON 0H 2 -2-thienyl 3.179 1 ON 0 0
H
3.180 1 ON 0 6
H
4 -4-0H 3 3.181 1 ON 0 6
H
4 -4-00H 3 3.182 1 ON 0 6
H
4 -4-OI 3.183 1 ON 0 6
H
4 -4-N0 2 3.184 1 ON OH 2 OH--0H 2 3.185 1 ON CH 2
O-=CH
3.186 1 ON OH 2 CH=-CHCsHs 3.187 1 ON CH 2
C=-OO
6 Hs 3.188 2 ON OH 3 3.189 2 ON 0 2
H
3.190 2 ON n-C 3
H
7 3.191 2 ON i-O 3
H
7 3.192 2 ON n-0 4 Hq 3.193 2 ON t-C 4 Hq 49 3.194 2 CN CYCIO-C 3 Hs 3.195 2 CN 0H 2 0 6
H
3.196 2 ON 0H 2
C
6
H
4 -4-CH 3 3.197 2 ON 0H 2
COH
4 -4-00H 3 3.198 2 ON 0H 2
COH
4 -4-Ot 3.199 2 ON 0H 2 0 6
H
4 -4-N0 2 3.200 2 ON CH 2 -2-turyl 3.201 2 ON CH 2 -2-thienyl 3.202 2 ON CAH 3.203 2 ON C 6
H
4 -4-OH 3 3.204 2 ON 0 6
H
4 -4-00H 3 3.205 2 ON 0 6
H
4 -4-OI 3.206 2 ON 0 6
H
4 -4-N0 2 3.207 2 ON OH 2 OH=0H 2 3.208 2 ON CH 2
O=-OH
3.209 2 ON CH 2 OHOCHC Hs 3.210 2 CN CH 2 C-=CCGHs 3.211 0 ON OH 2
SOH
3 3.212 0 ON 0H 2 S0 2
H
3.213 0 ON OH 2 S-n-0 3
H
7 3.214 0 ON OH 2 S-i-C 3
H
7 3.215 0 ON OH 2 S-n-O.H 9 3.216 0 ON OH 2 S-t-0 4
H
9 3.217 0 ON OH 2 S-CYClO-0 3
H
3.218 0 ON 0H 2 S0H 2 0 6 Hs 3.219 0 ON 0H 2 S0H 2 0 6
H
4 -4-0H 3 3.220 0 ON 0H 2 S0H 2 0 6
H
4 -4-00H 3 3.22 1 0 ON CH 2
SOH
2
O
6
H
4 -4-OI 3.222 0 ON 0H 2 S0H 2 0 6
H
4 -4-N0 2 3.223 0 ON OH 2
SOH
2 -2-furyl 3.224 0 ON OH 2 SOHr2-thienyl 3.225 0 ON 0H 2 S0 6
H
3.226 0 ON CH 2
SC
6
H
4 -4-0H 3 3.227 0 ON 0H 2 S0 6
H
4 -4-OCH 3 3.228 0 CN CH 2
SC
6
H
4 -4-Cl 3.229 0 ON CH 2
SC
6
H
4 -4-N0 2 3.230 0 ON OH 2
SOH
2 CH--0H 2 3.231 0 ON CH 2
SCH
2
C=-CH
3.232 0 ON OH 2
SOH
2 OH--OHCeH 3.233 0 ON CH 2
SCH
2 C-=CC6Hs 3.234 0 ON CH 2
NCN
N N N OH 3 Table 4 (O)n
NN
H
3
C
Compound n Y R 6 Physical data No.
4.1 0 NO 2
OH
3 4.2 0 NO 2 0 2 Hs 4.3 0 NO 2 n-0 3
H-
7 4.4 0 NO 2 i-0 3
H-
7 0 NO 2 n-C 4 Hg1 4.6 0 NO 2 t-0 4
H
9 4.7 0 NO 2 CYClo-0 3
H-
4.8 0 NO 2 0H 2 0 6
H
4.9 0 NO 2 0H 2 0 6
H
4 -4-0H 3 4.10 0 NO 2 0H 2 0 6
H
4 -4-OCH 3 -51 4.11 0 NO 2
CH
2
C
6
H
4 -4-CI 4.12 0 NO 2
CH
2
C
6
H
4 -4-N0 2 4.13 0 N0 2
CH
2 -2-furyl 4.14 0 NO 2
CH
2 -2-thienyl 4.15 0 NO 2
C
6 Hs 4.16 0 NO 2 CsH 4 -4-CH3 4.17 0 NO 2
C
6
H
4 -4-00H 3 4.18 0 NO 2
C
6
H
4 -4-CI 4.19 0 NO 2
C
6
H
4 -4-N0 2 4.20 0 NO 2
CH
2
CH=CH
2 4.21 0 NO 2
CH
2
C=-CH
4.22 0 NO 2
CH
2
CH=OCHC
6 Hs 4.23 0 NO 2
CH
2
C-=CC
6
H
4.24 0 NO 2
SCH
3 4.25 0 NO 2
SC
2 Hs 4.26 0 NO 2 S-n-C 3
H
7 4.27 0 NO 2 S-i-C 3
H
7 4.28 0 NO 2 S-n-C 4
H
9 4.29 0 NO 2 S-t-C 4
H
9 4.30 0 NO 2
S-CYCIO-C
3
H
4.31 0 NO 2
SCH
2
C
6 Hs 4.32 0 NO 2
SCH
2
C
6
H
4 -4-0H 3 4.33 0 NO 2
SCH
2
C
6
H
4 -4-00H3 4.34 0 NO 2
SCH
2 C6H 4 -4-CI 4.35 0 NO 2
SCH
2
C
6
H
4 -4-N0 2 4.36 0 NO 2
SCH
2 -2-furyl 4.37 0 NO 2
SCH
2 -2-thienyl 4.38 0 NO 2
SC
6
H
4.39 0 NO 2
SC
6 H4-4-CH 3 4.40 0 NO 2
SC
6
H
4 -4-00H 3 4.41 0 NO 2
SC
6
H
4 -4-CI 4.42 0 NO 2
SC
6
H
4 -4-N0 2 4.43 0 NO 2
SCH
2
CH=CH
2 52- 4.44 4.45 4.46 4.47 4.48 4.49 4.50 4.51 4.52 4.53 4.54 4.55 4.56 4.57 4.58 4.59 4.60 4.61 4.62 4.63 4.64 4.65 4.66 4.67 4.68 4.69 4.70 4.71 4.72 o NO 2
SCH
2
C-=CH
0 NO 2
SCH
2
CH=-CHC
6
H
0 NO 2
SCH
2
C=-CC
6 0 NO 2 NN02
H
3
C
1 NO 2
CH
3 1 NO 2
C
2 Hs 1 NO 2 n-C 3
H
7 1 NO 2 i-C 3
H
7 1 NO 2 n-C4H 9 1 NO 2 t-C 4
H
9 1 NO 2 CYClO-C 3 1 NO 2
CHACH
1 NO 2
CH
2
C
6
H
4 -4-CH 3 1 NO 2
CH
2
C
6
H
4 -4-OCH 3 1 NO 2
CH
2
C
6
H
4 -4-CI 1 NO 2
CH
2
C
6
H
4 -4-N0 2 1 NO 2
CH
2 -2-furyl 1 NO 2
CH
2 -2-thienyl 1 NO 2
C
6
H
1 NO 2
C
6
H
4 -4-CH 3 1 NO 2
C
6
H
4 -4-OCH 3 1 NO 2
C
6
H
4 -4-CI 1 NO 2
C
6
H
4 -4-N0 2 1 NO 2
CH
2 CH=0H 2 1 NO 2
CH
2
C--CH
1 NO 2
CH
2
CH=CHC
6
H
1 NO 2
CH
2
C-=CC
6
H
2 NO 2
CH
3 2 NO 2
C
2
H
53 4.73 2 NO 2 n-C 3
H
7 4.74 2 NO 2 i-C 3
H
7 4.75 2 NO 2 .n-C 4 H9 4.76 2 NO 2 t-0 4
H
9 4.77 2 NO 2 CYCIO-0 3 Hs 4.78 2 NO 2 4.79 2 NO 2
CH
2
COH
4 -4-0H 3 4.80 2 NO 2
CH
2
C
6
H
4 -4-OCH 3 4.81 2 NO 2
CH
2
C
6
H
4 -4-O 4.82 2 NO 2
CH
2
C
6
H
4 -4-NO 2 4.83 2 NO 2
CH
2 -2-furyt 4.84 2 NO 2
CH
2 -2-thienyl 4.85 2 NO 2
CAH
4.86 2 NO 2
C
6
H
4 -4-0H 3 4.87 2 NO 2
C
6
H
4 -4-OCH 3 4.88 2 NO 2
C
6
H
4 -4-CI 4.89 2 NO 2 CGH4-4-N0 2 4.90 2 NO 2
CH
2 CH=0H 2 4.91 2 NO 2
CH
2
C=CH
4.92 2 NO 2
CH
2
CH=CHC
6
HS
4.93, 2 NO 2
CH
2
C-=CC
6
H
4.94 0 NO 2
CH
2
SCH
3 4.95 0 NO 2
CH
2
SC
2 Hs 4.96 0 NO 2
CH
2 S-n-C 3
H
7 4.97 0 NO 2
CH
2 S-i-C 3
H
7 4.98 0 NO 2
CH
2 S-n-C 4 H9 4.99 0 NO 2
CH
2 S-t-C4H 9 4.100 0 NO 2
CH
2 S-CYClO-C 3
H
4.101 0 NO 2
CH
2
SCH
2
C
6
H
4.102 0 NO 2
CH
2
SCH
2
C
6 H4-4-CH 3 4.103 0 NO 2
CH
2
SCH
2
C
5
H
4 -4-OCH 3 4.104 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CI 4.105 0 NO 2
CH
2
SCH
2
C
6 H4-4-N0 2 -54 4.106 0 NO 2
CH
2
SCH
2 -2-furyl 4.107 0 NO 2
OH
2
SCH
2 -2-thienyl 4.108 0 NO 2
CH
2
SC
6 Hs 4.109 0 NO 2
OH
2
SC
6 H4-4-CH 3 4.110 0 NO 2
CH
2 SCsH 4 -4-00H 3 4.111 0 NO 2
CH
2
SC
6
H
4 -4-CI 4.112 0 NO 2
CH
2
SC
6
H
4 -4-N0 2 4.113 0 NO 2
OH
2
SCH
2
CH=CH
2 4.114 0 NO 2
CH
2
SOH
2
C=-OH
4.115 0 NO 2
CH
2
SCH
2 CH=0CH 6 Hs 4.116 0 NO 2
CH
2
SCH
2
C-=OC
6 Hs 4.117 0 NO 2 CH2 sN
N
NN
H
3
C
4.118 0 CN OH 3 4.119 0 ON C 2
H
4.120 0 CN n-C 3
H
7 4.121 0 ON i-C 3
H
7 4.122 0 ON n-C 4
H
9 4.123 0 ON t-C 4
H
9 4.124 0 ON CYClo-OaH6 4.125 0 ON 0H 2 CsHs 4.126 0 ON 0H 2 0 6
H
4 -4-0H 3 4.127 0 ON 0H 2 0 6
H
4 -4-00H 3 4.128 0 ON CH 2 0 6
H
4 -4-OI 4.129 0 ON 0H 2 0 6
H
4 -4-N0 2 4.130 0 CN CH 2 -2-furyl 4.131 0 ON 0H 2 -2-thienyl 4.132 0 ON C 6
H
4.133 0 ON C 6
H
4 -4-CH 3 4.134 140 ON C 6
H
4 -4-OCH 3 4.135 0 CN C 6
H
4 -4-CI 4.136 0 ON 0 8
;H
4 -4-N0 2 4.137 0 ON CH 2 CH=0CH 2 4.138 0 ON CH 2
O=-OH
4.139 0 ON OH 2 CH=OCH~eH 4.140 0 ON CH 2
O,-OO
6 Hs 4.141 0 ON SOH 3 4.142 0 ON S0 2 Hs 4.143 0 ON S-n-C 3
H
7 4.144 0 ON S-i-C 3
H
7 4.145 0 CN S-n-C 4 H9 4.146 0 ON S-t-0 4
H
9 4.147 0 ON S-CYCIO-0 3
H
4.148 0 ON S0H 2 0 6
H
4.149 0 ON S0H 2 0 6
H
4 -4-0H 3 4.150 0 ON SOH 2
O
6
H
4 -4-00H 3 4.151 0 ON S0H 2 0 6
H
4 -4-CI 4.152 0 ON S0H 2 0 6
H
4 -4-N0 2 4.153 0 ON SOH 2 -2-furyl 4.154 0 ON SOH 2 -2-thienyl 4.155 0 ON S0 6
H
4.156 0 ON S0 6
H
4 -4-0H 3 4.157 0 ON SO 6 H4-4-00H 3 4.158 0 ON S0 5
H
4 -4-OI 4.159 0 ON S0 6
H
4 -4-N0 2 4.160 0 ON SOH 2
OH=OCH
2 4.161 0 ON SCH 2
O-=OH
4.162 0 ON SCH 2 CH=0CHC 6 Hs 4.163 4630 ON SCH 2 C--C~rHs -56 4.164 0 CN sN~oN N J1 NJ CH3
N
H
3
C
4.165 1 ON OH 3 4.166 1 CN 0 2 Hs 4.167 1 ON n-0 3
H
7 4.168 1 ON i-0 3
H
7 4.169 1 ON n-C 4
H
9 4.170 1 ON t-C 4
H
9 4.171 1 ON CYClO-0 3
H
4.172 1 ON 0H 2 0 6
H
4.173 1 ON 0H 2
C
6
H
4 -4-0H 3 4.174 1 ON OH 2 0 6
H
4 -4-OCH 3 4.175 1 ON 0H 2 0 6
H
4 -4-OI 4.176 1 ON 0H 2
O
6
,H
4 -4-N0 2 4.177 1 ON 0H 2 -2-furyl 4.178 1 ON 0H 2 -2-thienyl 4.179 1 ON CAH 4.180 1 ON 0 6
H
4 -4-0H 3 4.181 1 ON 0 6
H
4 -4-00H 3 4.182 1 ON 0 6
H
4 -4-OI 4.183 1 ON 0 6
H
4 -4-N0 2 4,184 1 ON OH 2 OH=0CH 2 4.185 1 ON OH 2
O-=OH
4.186 1 ON OH 2 OH=0CH0 8
H
4.187 1 ON OH 2 OEO-CeH 4.188 2 ON OH 3 4.189 2 ON 0 2
H
4.190 2 ON n-0 3
H
7 4.191 2 ON i-0 5
H
7 4.192 2 ON n-C 4
H
9 -57 4.193 2 ON t-C 4
H
9 4.194 2 ON CYClO-C 3
H
4.195 2 ON CH 2
C
6
H
4.196 2 ON CH 2
C
6
H
4 -4-CH 3 4.197 2 ON 0H 2 CsH 4 4-00H 3 4.198 2 ON CH 2
C
6
H
4 -4-CI 4.199 2 ON CH 2
O
6
H
4 -4-N0 2 4.200 2 ON OH 2 -2-furyl 4.201 2 ON 0H 2 -2-thienyl 4.202 2 ON 0 6 Hs 4.203 2 ON 0 6
H
4 -4-0H 3 4.204 2 ON 0 6
H
4 -4-00H 3 4.205 2 ON 0 6
H
4 -4-OI 4.206 2 ON 0 6
H
4 -4-N0 2 4.207 2 ON OH 2 OH=0CH 2 4.208 2 ON CH 2
O-=OH
4.209 2 CN CH- 2
CH=-CHC
6 Hs 4.210 2 ON CH 2
O=-OC
6 Hs 4.211 0 ON OH 2
SOH
3 4.212 0 ON 0H 2 S0 2
H
4.213 0 ON CH 2 S-n-0 3
H
7 4.214 0 ON CH 2 S-i-0 3
H
7 4.215 0 ON OH 2 S-n-0 4
H
9 4.216 0 ON OH 2 S-t-C 4
H
9 4.217 0 ON CH 2 S-CYClO- 3
H
4.218 0 ON CH 2
SOH
2
C
6
H
4.219 0 ON CH 2
SCH
2
C
6 H4-4-0H 3 4.220 0 ON CH 2
SCH
2
C
6
H
4 -4-00H 3 4.221 0 ON OH 2
SOH
2
O
6
H
4 -4-OI 4.222 0 ON 0H 2 S0HA0H 4 -4-N0 2 4.223 0 ON OH 2
SOH
2 -2-furyl 4.224 0 ON CH 2
SCH
2 -2-thienyl 4.225 450 ON CH 2
SC
6 Hs 58.- 4.226 0 CN CH 2
SC
6
H
4 -4-0H 3 4.227 0 CN CH 2 S0 6
H
4 -4-00H 3 4.228 0 ON CH 2
SC
6
H
4 -4-Cl 4.229 0 ON CH 2 SCeH 4 -4-N0 2 4.230 0 ON CH 2
SCH
2
CH=-CH
2 4.231 0 ON CH 2
SCH
2
O.OH
4.232 0 CN OH 2
SOH
2
CH=OCHC
6
H
4.233 0 ON CH 2
SCH
2
OCOC
6 Hs 4.234 0 ON CH 2 N' ON N
N,
H
3
C
Table
N
Compound No. n Y R6Phys. data 5.1 0 NO 2
OH
3 5.2 0 NO 2
C
2 Hs 5.3 0 NO 2 n-C 3
H
7 5.4 0 NO 2 i-0 3
H
7 0 NO 2 flC 4 Hg 5.6 0 NO 2 t-0 4
H
9 5.7 0 NO 2 CYClO-0 3
H
5.8 0 NO 2 0H 2 0 6 Hs 5.9 0 NO 2 0H 2 0 6
H
4 -4-0H 3 5.10 0 NO 2 0H 2 0 6
H
4 -4-OCH 3 5.11 0 NO 2
CH
2 C6H 4 -4-CI 59 5.12 0 NO 2
CH
2 0 6
H
4 -4-NO 2 5.13 0 NO 2
CH
2 -2-furyl 5.14 0 NO 2
CH
2 -2-thienyl 5.15 0 NO 2
C
6
H
5.16 0 NO 2
C
8
H
4 -4-0H 3 5.17 0 NO 2
C
6
H
4 -4-OCH 3 5.18 0 NO 2
C
6
H
4 -4-CI 5.19 0 NO 2
C
6
H
4 -4-N0 2 5.20 0 NO 2
CH
2
CH=CH
2 5.21 0 NO 2
CH
2
C-=CH
5.22 0 NO 2
CH
2
CH=CHC
6 5.23 0 NO 2
CH
2
C=-CC
6
H
5.24 0 NO 2
SCH
3 5.25 0 NO 2
SC
2
H
5.26 0 NO 2 S-n-C 3
H
7 5.27 0 NO 2 S-i-C 3
H
7 5.28 0 NO 2 S-n-C 4
H
9 5.29 0 NO 2 S-t-C 4
H
9 5.30 0 NO 2 S-CYClO-C 3 Hs 5.31 0 NO 2
SCH
2
C
6 Hs 5.32. 0 NO 2
SCH
2
C
6
H
4 -4-0H 3 5.33 0 NO 2
SCH
2 CrH 4 -4-OCH 3 5.34 0 NO 2
SCH
2
C
6
H
4 -4-CI 5.35 0 NO 2
SCH
2
C
6
H
4 -4-N0 2 5.36 0 NO 2
SCH
2 -2-furyt 5.37 0 NO 2
SCH
2 -2-thienyl 5.38 0 NO 2 SC6Hs 5.39 0 NO 2 SCrH 4 -4-CH 3 5.40 0 NO 2
SC
6
H
4 -4-OCH 3 5.41 0 NO 2
SC
6
H
4 -4-CI 5.42 0 NO 2
SC
6
H
4 -4-N0 2 5.43 0 NO 2
SCH
2 CH=0CH 2 5.44 0 NO 2
SCH
2
C-=CH
5.45 0 NO 2
SCH
2
CH=-CHC
6
H
5.46 0 NO 2
SCH
2
C-CC
6 Hs 5.47 0 NO 2 5.48 1 NO 2
CH
3 5.49 1 NO 2
C
2 Hs 5.50 1 NO 2 n-0 3
H
7 5.51 1 NO 2 i-C 3
H
7 5.52 1 NO 2 n-C 4
H
9 5.53 1 NO 2 t-0 4
H
9 5.54 1 NO 2 CYClO-C 3 Hs 5.55 1 NO 2
CH
2
C
6 Hs 5.56 1 NO 2
CH
2
C
6
H
4 -4-CH 3 5.57 1 NO 2
CH
2
C
6
H
4 -4-OCH 3 5.58 1 NO 2
CH
2
C
6
H
4 -4-CI 5.59 1 NO 2
CH
2
C
6
H
4 -4-N0 2 5.60 1 NO 2
CH
2 -2-furyl 5.61 1 NO 2 0H 2 -2-thienyl 5.62, 1 NO 2
C
6
H
5.63 1 NO 2
C.H
4 -4-CH 3 5.64 1 NO 2
C
6
H
4 -4-OCH 3 5.65 1 NO 2 CsH 4 -4-OI 5.66 1 NO 2
C
6
H
4 4-N0 2 5.67 1 NO 2
CH
2 CH=0CH 2 5.68 1 NO 2
CH
2
C-=CH
5.69 1 NO 2
CH
2
CH=-CHC
6
H
5.70 1 NO 2
CH
2
C=-OC
6
H
5.71 2 NO 2
CH
3 5.72 2 NO 2
CAH
5.73 2 NO 2 n-C 3
H
7 5.74 2 NO 2 i-C 3
H
7 -61- 5.75 2 NO 2 n-0 4
H
9 5.76 2 NO 2 t-C 4
H
9 5.77 2 NO 2 cyclo-C 3 Hs 5.78 2 NO 2
CH
2 5.79 2 NO 2
CH
2
C
6
H
4 -4-0H 3 5.80 2 NO 2
CH
2
C.H
4 -4-OCH 3 5.81 2 NO 2
CH
2
C
6
H
4 -4-CI 5.82 2 NO 2
CH
2
C
6
H
4 -4-NO 2 5.83 2 NO 2
CH
2 -2-furyl 5.84 2 NO 2
CH
2 -2-thienyl 5.85 2 NO 2 C6Hs 5.86 2 NO 2
C
6
H
4 -4-CH 3 5.87 2 NO 2
C
6
H
4 -4-OCH 3 5.88 2 NO 2 C6H 4 -4-CI 5.89 2 NO 2
C
6
H
4 -4-N0 2 5.90 2 NO 2
CH
2
CH=CH
2 5.91 2 NO 2
CH
2
C=-CH
5.92 2 NO 2
CH
2
CH--OHC
6
H
5.93 2 NO 2
CH
2 CmCC 6
H
5.94 0 NO 2
CH
2
SCH
3 5.95 0 NO 2
CH
2
SC
2
H
5.96 0 NO 2
CH
2 S-n-C 3
H
7 5.97 0 NO 2
CH
2 S-i-CH 7 5.98 0 NO 2
CH
2 S-n-C 4
H
9 5.99 0 NO 2
CH
2 S-t-C 4
H
9 5.100 0 NO 2
CH
2 S-CYClo-C 3
H
5.101 0 NO 2
CH
2
SCH
2
C
6
H
5.102 0 NO 2
CH
2
SCH
2 CoH 4 -4-CH 3 5.103 0 NO 2
CH
2
SCH
2
C
6 H4-4-OCH 3 5.104 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CI 5.105 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-N0 2 5.106 0 NO 2
CH
2
SCH
2 -2-furyl 5.107 0 NO 2
CH
2
SCH
2 -2-thienyl 62 5.108 0 NO 2
CH
2 S0 6 Hs 5.109 0 NO 2
CH
2
SC
6
H
4 -4-CH 3 5.110 0 NO 2
OH
2
SC
6
H
4 -4-OCH 3 5.111 0 NO 2
CH
2 SCeH 4 -4-CI 5.112 0 NO 2
CH
2 SCeH 4 -4-N0 2 5.113 0 NO 2
CH
2
SCH
2 CH--0H 2 5.114 0 NO 2
CH
2
SCH
2 Ca-CH 5.115 0 NO 2
CH
2
SCH
2
CH=CHC
6
H
5.116 0 NO 2
CH
2
SCH
2
C=-CO
6 Hs 5.117 0 NO 2
OH
2 N'N0 2 s6 5.118 0 ON CH 3 5.119 0 ON C 2 Hs 5.120 0 ON n-C 3
H
7 5.121 0 ON i-C 3
H
7 5.122 0 ON n-C 4
H
9 5.123 0 ON t-0 4
H
9 5.124 0 ON CYClO-0 3
H
5.125 0 ON 0H 2 0 6 Hs 5.126 0 ON 0H 2
C
6
H
4 -4-CH 3 5.127 0 ON 0H 2 0 6
H
4 -4-00H 3 5.128 0 CN 0H 2 0 6
H
4 -4-Oi 5.129 0 ON 0H 2
C
6
H
4 -4-N0 2 5.130 0 ON 0H 2 -2-furyl 5.131 0 ON 0H 2 -2-thienyl 5.132 0 ON 0 6
H
5.133 0 ON 0 6
H
4 -4-0H 3 5.134 0 ON C 6
H
4 -4-00H 3 5.135 0 ON 0 6
H
4 -4-OI 5.136 0 ON 0 6
H
4 -4-N0 2 5.137 0 ON CH 2
CH=CH
2 -63 5.138 0 ON CH 2
O-=CH
5.139 0 ON CH 2
CH=CHC
6 Hs 5.140 0 ON CH 2
C-=CC
6 Hs 5.141 0 ON SOH 3 5.142 0 ON S0 2 Hs 5.143 0 ON S-n-0 3 H7 5.144 0 ON S-i-0 3
H
7 5.145 0 ON S-n-0 4 H9 5.146 0 ON S-t-0 4
H
9 5.147 0 ON S-CYClO-O 3 Hs 5.148 0 ON S0H 2 0 6
H
5.140 0 ON S0H 2 0 6
H
4 -4-0H 3 5.150 0 ON S0H 2 0 6
H
4 -4-00H 3 5.151 0 ON S0H 2 0 6
H
4 -4-OI 5.152 0 ON S0H 2 0 6
H
4 -4-N0 2 5.153 0 ON SCH 2 -2-furyl 5.154 0 ON SCH 2 -2-thieriyl 5.155 0 ON S0 6
H
5.156 0 ON S0 6
H
4 -4-0H 3 5.157 0 ON SC 6
H
4 -4-00H 3 5.158 0 ON S0 6
H
4 -4-OI 5.159 0 ON SC 6 H4-4-N0 2 5.160 0 ON SOH 2 OH=0H 2 5.161 0 ON SCH 2 CsCH 5.162 0 ON SCH 2
OH=OHC
6
H
5.163 0 CN SCH 2
C-=OO.H
5.164 0 CN S< 'C
NN-C
5.165 1 ON OH 3 5.166 1 ON 0 2 Hs 5.167 1 ON n-C 3
H
7 64- 5.168 1 ON i-C 3
H
7 5.169 1 CN n-0 4
H
9 5.170 1 ON t-C 4 H9 5.171 1 ON CYClo-0 3 Hs 5.172 1 ON CH 2
C
6
H
5.173 1 ON 0H 2 0 6
H
4 -4-0H 3 5.174 1 CN 0H 2
O
6
H
4 -4-OCH 3 5.175 1 ON 0H 2 0 6
H
4 -4-Ot 5.176 1 ON CH 2 0 6
H
4 -4-N0 2 5.177 1 ON OH 2 -2-furyl 5.178 1 ON 0H 2 -2-thienyl 5.179 1 ON CAH 5.180 1 ON 0 6
H
4 -4-0H 3 5.181 1 ON 0 6
H
4 -4-00H 3 5.182 1 ON 0 6
H
4 -4-OI 5.183 1 ON 0 6
H
4 -4-N0 2 5.184 1 ON OH 2 OH--1H 2 5.185 1 ON CH 2
O-=OH
5.186 1 ON OH 2
OH=OCHO
6 Hs 5.187 1 ON CH 2
C-=CC
6
H
5.188 2 ON -0H 3 5.189 2 ON C 2
H
5.190 2 ON n-0 3
H
7 5.191 2 ON i-0 3
H
7 5.192 2 ON n-0 4 Hq 5.193 2 ON t-0 4 Hq 5.194 2 ON CYCI0-0 3
H
5.195 2 ON CH 2 0 6
H
5.196 2 ON C0H 2 0 6
H
4 -4-0H 3 5.197 2 ON 0H 2 0 6
H
4 -4-00H 3 5.198 2 ON CH 2 0 6
H
4 -4-OI 5.199 2 ON 0H 2 0 6
H
4 -4-N0 2 5.200 2 ON CH 2 -2-furyl 5.201 2 ON CH 2 -2-thienyt 5.202 2 ON C 6
H
5.203 2 ON C 6
H
4 -4-0H 3 5.204 2 ON C 6
H
4 -4-00H 3 5.205 2 ON C 6
H
4 -4-CI 5.206 2 ON 0 6
H
4 -4-N0 2 5.207 2 ON OH 2 OH=0CH 2 5.208 2 ON CH 2
C-=OH
5.209 2 ON OH 2 OH=CHC6H 5.210 2 ON CH 2
C-=CC
6 Hs 5.211 0 ON OH 2
SOH
3 5.212 0 ON 0H 2 S0 2
H
5.213 0 ON OH 2 S-n-0 3
H
7 5.214 0 ON OH 2 S-i-0 3
H
7 5.215 0 ON OH 2 S-n-0 4
H
9 5.216 0 ON OH 2 S-t-O.H 9 5.217 0 ON OH 2 S-CYClO-0 3 Hs 5.218 0 ON 0H 2 S0H 2 0 6
H
5.219 0 ON 0H 2 S0H 2 0 6
H
4 -4-C;H 3 5.220 0 ON 0H 2 S0H 2 0 6
H
4 -4-00H 3 5.221 0 ON OH 2
SOH
2
O
6 H4-4-CI 5.222 0 ON 0H 2 S0H 2 0 6
H
4 -4-N0 2 5.223 0 ON OH 2
SOH
2 -2-furyl 5.224 0 ON CH 2
SOH
2 -2-thienyl 5.225 0 ON 0H 2 S0 6
H
5.226 0 ON CH 2
SO
6
H
4 -4-0H 3 5.227 0 ON CH 2
SO
6
H
4 -4-00H 3 5.228 0 ON 0H 2 S0 6
H
4 -4-OI 5.229 0 ON 0H 2 S0 6
H
4 -4-N0 2 5.230 0 ON CH 2
SOH
2 OH=0H 2 5.231 0 ON OH 2
SCH
2
O-=OH
5.232 0 ON OH 2
SOH
2
OH=OHO
6 5.233 0 ON CH 2
SCH
2
O=-CC
6 Hs 66 5.234 0 ON OH 2
C
N
Table 6 Compound No. n Y Rs Phys. data 6.1 0 NO 2
OH
3 6.2 0 NO 2 0 2 Hs 6.3 0 NO 2 n-0 3
H
7 6.4 0 NO 2 i-0 3
H
7 0 NO 2 n-0 4
H
9 6.6 0 NO 2 t-0 4
H
9 6.7 0 NO 2 CYClO-0 3
H
6.8 0 NO 2 0H 2 0 6 Hs 6.9 0 NO 2 0H 2 0 6
H
4 -4-0H 3 6.10 0 NO 2 0H 2 0.H 4 -4-00H 3 6.11 0 NO 2 0H 2 0 6
H
4 -4-OI 6.12 0 NO 2 0H 2 0 6
H
4 -4-N0 2 6.13 0 NO 2 0H 2 -2-furyl 6.14 0 NO 2 0H 2 -2-thienyl 6.15 0 NO 2
CAH
6.16 0 NO 2 0 6
H
4 -4-0H 3 6.17 0 NO 2 0 6
H
4 -4-00H 3 6.18 0 NO 2 0 6
H
4 -4-CI 6.19 0 NO 2 0 6
H
4 -4-N0 2 6.20 0 NO 2
OH
2 CH=0H 2 67 6.21 0 NO 2
CH
2
CEOCH
6.22 0 NO 2
CH
2 6.23 0 NO 2
CH
2
C-=CC
6 Hs 6.24 0 NO 2
SCH
3 6.25 0 NO 2
SC
2 Hs 6.26 0 NO 2 S-n-C 3
H
7 6.27 0 NO 2 S-i-C 3
H
7 6.28 0 NO 2 S-n-C 4 Hg 6.29 0 NO 2 S-t-C 4 Hq 6.30 0 NO 2 S-CYClO-C 3 6.31 0 NO 2
SCH
2 CcHs 6.32 0 NO 2
SCH
2
C
6
H
4 -4-CH3 6.33 0 NO 2
SCH
2
C
6
H
4 -4-OCH3 6.34 0 NO 2
SCH
2
C
6
H
4 -4-CI 6.35 0 NO 2
SCH
2 C6H 4 -4-N02 6.36 0 NO 2
SCH
2 -2-furyl 6.37 0 NO 2
SCH
2 -2-thienyl 6.38 0 NO 2
SC
6
H
6.39 0 NO 2
SC
6
H
4 -4-CH 3 6.40 0 NO 2
SC
6
H
4 -4-OCH3 6.41 0 NO 2
SC
6
H
4 -4-CI 6.42 0 NO 2
SC
6
H
4 -4-N0 2 6.43 0 NO 2
SCH
2
CH=CH
2 6.44 0 NO 2
SCH
2
C-CH
6.45 0 NO 2
SCH
2
CH=-CHC
6 6.46 0 N0 2
SCH
2
C=OC
6 Hs 6.47 0 NO 2 6.48 1 NO 2
OH
3 6.49 1 NO 2
CAH
6.50 1 NO 2 n-C 3
H
7 68- 6.51 1 NO 2 i-C 3
H
7 6.52 1 NO 2 n-C 4 H9 6.53 1 NO 2 t-C 4 H9 6.54 1 NO 2 cyclo-C 3 Hs 6.55 1 NO 2
CH
2
CH
6.56 1 NO 2
CH
2 0 6
H
4 -4-CH 3 6.57 1 NO 2
CH
2 C.R4OCH3 6.58 1 NO 2
CH
2
C
6
H
4 -4-CI 6.59 1 NO 2
CH
2 0 6
H
4 -4-N0 2 6.60 1 NO 2
CH
2 -2-furyl 6.61 1 NO 2
CH
2 -2-thienyl 6.62 1 NO 2
C
6 Hs 6.63 1 NO 2 0 8
H
4 -4-CH 3 6.64 1 NO 2
CGH
4 -4-OCH 3 6.65 1 NO 2
C
6
H
4 -4-CI 6.66 1 NO 2 CrH 4 -4-N0 2 6.67 1 NO 2
CH
2
CH=-CH-
2 6.68 1 NO 2
CH
2
C=-CH
6.69 1 NO 2
CH
2 CH=CHCoHs 6.70 1 NO 2
CH
2
C=-CC
6
H
6.71 2 NO 2
CH
3 6.72 2 NO 2
C
2 Hs 6.73 2 NO 2 n-C 3
H
7 6.74 2 NO 2 i-C 3
H
7 6.75 2 NO 2 n-C 4
H
9 6.76 2 NO 2 t-C 4 H9 6.77 2 NO 2 CYClO-C 3 Hs 6.78 2 NO 2
CH
2
C
6 Hs 6.79 2 NO 2
CH
2
C
6
H
4 -4-CH 3 6.80 2 NO 2
CH
2
C
6
H
4 -4-OCH3 6.81 2 NO 2 0H 2 0 6
H
4 -4-Cl 6.82 2 NO 2
CH
2
C
6
H
4 -4-N0 2 6.83 2 NO 2
CH
2 -2-furyl -69 6.84 2 NO 2
CH
2 -2-thienyl 6.85 2 NO 2
C
6 Hs 6.86 2 NO 2
C
6
H
4 -4-CH 3 6.87 2 NO 2 0 6
H
4 -4-OCH 3 6.88 2 NO 2
C
6
H
4 -4-Cl 6.89 2 NO 2
C
6
H
4 -4-N0 2 6.90 2 NO 2
CH
2
CH=CH
2 6.91 2 NO 2
CH
2
C=-CH
6.92 2 NO 2
CH
2 CH=-CHC6Hs 6.93 2 NO 2
CH
2 C=-CCsHs 6.94 0 N0 2
CH
2
SCH
3 6.95 0 NO 2
CH
2
SC
2 Hs 6.96 0 NO 2
CH
2 S-n-C 3
H
7 6.97 0 NO 2
CH
2 S-i-CH 7 6.98 0 NO 2
CH
2 S-n-0 4
H
9 6.99 0 NO 2
CH
2 S-t-C 4
H
9 6.100 0 NO 2
CH
2
S-CYCIO-C
3 6.101 0 NO 2 .eCH 2 6.102 0 NO 2
CH
2
SCH
2
CBH
4 -4-0H3 6.103 0 NO 2
CH
2
SCH
2 C6H 4 -4-OCH3 6.104 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CI 6.105 0 NO 2
CH
2
SCH
2 CeH 4 -4-N0 2 6.106 0 NO 2
CH
2
SCH
2 -2-furyl 6.107 0 NO 2
CH
2
SCH
2 -2-thienll 6.108 0 NO 2
CH
2 SC6Hs 6.109 0 NO 2
CH
2
SC
8
H
4 -4-0H 3 6.110 0 NO 2
CH
2
SC
6
H
4 -4-OCH 3 6.111 0 NO 2
CH
2
SC
6
H
4 -4-CI 6.112 0 NO 2 0CH 2
SC
6
H
4 -4-NO 2 6.113 0 NO 2
CH
2
SCH
2 CH=CH2 6.114 0 NO 2
CH
2
SCH
2
C-=CH
6.115 0 NO 2
CH
2
SCH
2
CH=-CHC
6
H
6.116 0 NO 2
.CH
2
SCH
2 C=-CC6H 6.117 0 NO 2
OH
2 N-0 s N- :1 6.118 0 ON OH 3 6.119 0 ON C 2
H
6.120 0 ON n-C 3
H
7 6.121 0 CN i-C 3
H
7 6.122 0 ON n-0 4 Hq 6.123 0 ON t-0 4 Hq 6.124 0 ON CYClO-OaH 6.125 0 ON CH 2
C
6 Hs 6.126 0 ON OH 2 0 6
H
4 -4-0H 3 6.127 0 ON 0H 2
C
6
H
4 -4-OOH 3 6.128 0 ON 0H 2 0 6
H
4 -4-OI 6.129 0 ON 0H 2 0 6
H
4 -4-N0 2 6.130 0 ON 0H 2 -2-furyl 6.1 31 0 ON 0H 2 -2-thienyt 6.132 0 ON 0 6 Hs 6.133 0 ON 0 6
H
4 -4-0H 3 6.134 0 ON 0 6
H
4 -4-00H 3 6.135 0 ON 0 6
H
4 -4-OI 6.136 0 ON 0 6
H
4 -4-N0 2 6.137 0 ON OH 2 OH--0H 2 6.138 0 ON CH 2
O=-OH
6.139 0 ON OH 2
OH=OCHC
6
H
6.140 0 ON CH 2
O-=OO
6
H
6.141 0 ON SOH 3 6.142 0 ON S0 2
H
6.143 0 ON S-n-0 3
H
7 6.144 0 ON S-i-0 3
H
7 6.145 0 ON S-n-0 4
H
9 6.146 0 ON S-t-0 4 Hq -71- 6.147 6.148 6.149 6.150 6.15 1 6.152 6.153 6.154 6.155 6.156 6.157 6.15e 6.159 6.160 6.161 6.162 6.163 6.164 0 ON 0 ON o ON 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON o ON 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON S-WCycO-C 3 S0HA0H
SCH
2 OeH 4 -4-0H3
SOH
2 CoH4-00OH3 S0HH 2 6 4 -4-CI SCHA0H4NO2
SCH
2 -2-turyl
SCH
2 -2-thienyl
SCAH
S0 6
H
4 -4-CH 3 SCsH 4 -4-OCH 3
SC
6
H
4 -4-OI S0 6
H
4 -4-N0 2
SCH
2
CH=CH
2
SCH
2
C-=CH
SCH
2
CH=OCHO
6 Hs
SCH
2 6.165 6.166 6.167 6.168 6.169 6.170 6.171 6.172 6.173 6.174 6.175 6.176 1 ON 1 ON 1 CN 1 ON 1 ON 1 ON 1 ON 1 ON 1 ON 1 ON 1 ON 1 ON
OH
3
C
2 Hs n-C 3
H
7 i-C 3
H
7 fl-OgHg t-C 4
H
9
CYCIO-C
3 Hs
CH
2
C
6 Hs
CH
2
C
6
H
4 -4-CH3
CH
2 C0 6
H
4 -4-00H 3
CH
2 CeH 4 -4-CI
CH
2
C
6
H
4 -4-N0 2 -72- 6.177 1 ON CH 2 -2-turyl 6.178 1 ON CH 2 -2-thienyl 6.179 1 ON 0 6
H
6.180 1 ON O 6 H4-4-OH 3 6.181 1 ON C 6
H
4 -4-00H 3 6.182 1 ON C6114-4-C1 6.183 1 ON C 6
H
4 -4-N0 2 6.184 1 ON OH 2 OH=0CH 2 6.185 1 ON OH 2
CEOCH
6.186 1 ON OH 2 OH=OCHceH 6.187 1 ON CH 2 0O=OO 6
H
6.188 2 ON OH 3 6.189 2 ON 0 2
H
6.190 2 ON n-0 3
H
7 6.191 2 ON i-0 3
H
7 6.192 2 ON n-0 4
H
9 6.193 2 ON t-0 4
H
9 6.194 2 ON CYClO-O 3
H
6.195 2 ON 0H 2 0 6 Hs 6.196 2 ON OH 2 0 6
H
4 -4-OH 3 6.197 2 ON 0H 2 C6H 4 -4-O0H 3 6.198 2 ON 0H 2 0 6
H
4 -4-OI 6.199 2 ON 0H 2 0 6
H
4 -4-N0 2 6.200 2 ON 0H 2 -2-furyt 6.201 2 ON 0H 2 -2-thienyl 6.202 2 ON 0 6
H
6.203 2 ON 0 6
H
4 -4-0H 3 6.204 2 ON 0 6 11 4 -4-00H 3 6.205 2 ON 0 6
H
4 -4-CI 6.206 2 ON 0 6
H
4 -4-N0 2 6.207 2 ON OH 2 OH=0H 2 6.208 2 ON CH 2
O-=OH
6.209 2 ON CH 2 CH=0CHC 6 Hs -73- 6.210 2 CN CHZC-=OC 6 Hs 6.211 0 ON CH 2
SCH
3 6.212 0 CN CH 2
SC
2 6.213 0 ON CH 2 S-n-C 3 H-l 6.214 0 ON CH 2 S-i-0 3
H
7 6.215 0 CN CH 2 S-n-O.H9 6.216 0 ON OH 2 S-t-0 4 H9 6.217 0 ON CH 2 S-cyc]o-C 3
H
6.218 0 ON CH 2
SCH
2 OeHs 6.219 0 ON CH 2
SOH
2
C
6
H
4 -4-0H 3 6.220 0 ON OH 2
SCH
2
O
6
H
4 -4-OCH 3 6.221 0 ON OH 2
SOH
2
O.H
4 -4-Cl 6.222 0 ON OH 2
SCH
2
C
6
H
4 -4-N0 2 6.223 0 ON CH 2
SCH
2 -2-furyl 6.224 0 ON OH 2
SCH
2 -2-thienyl 6.225 0 ON 0H 2 S0 6
H
6.226 0 ON CH 2
SC
6
H
4 -4-CH 3 6.227 0 ON 0H 2
SC
6
H
4 -4-00H 3 6.228 0 ON 0H 2 S0 6
H
4 -4-CI 6.229 0 ON OH 2
SO
6 H4-4-N0 2 6.230 0 ON CH 2
SCH
2 CH=0H 2 6.23 1 0 ON CH 2
SCH
2
C-=OH
6.232 0 ON CH 2
SOH
2
CH=OCHC
6 Hs 6.233 0 ON CH 2
SOH
2 OEOCCeHs 6.234 0 ON OH 2 N N 74- Table 7 Compound No. n Y R6Phys. data 7.1 0 NO 2
OH
3 7.2 0 NO 2
C
2 Hs 7.3 0 NO 2 n-C 3
H
7 7.4 0 NO 2 i-C 3 H7 0 NO 2 n-C 4 Hg 7.6 0 NO 2 t-C 4 Hq 7.7 0 NO 2 CYClO-C 3 7.8 0 NO 2
CH
2
C
6 Hs 7.9 0 NO 2
CH
2
C
6
H
4 -4-CH 3 7.10 0 NO 2
CH
2
C
6
H
4 -4-OCH 3 7.11 0 NO 2
CH
2
C
6
H
4 -4-Cl 7.12 0 NO 2
CH
2
C
6
H
4 -4-N0 2 7.13 0 NO 2
CH
2 -2-furyl 7.14, 0 NO 2
CH
2 -2-thienyl 7.15 0 NO 2
C
6
H
7.16 0 NO 2
C
6
H
4 -4-CH 3 7.17 0 NO 2
C
6
H
4 -4-OCH 3 7.18 0 NO 2 0 6
H
4 -4-Cl 7.19 0 NO 2
C
6
H
4 -4-N0 2 7.20 0 NO 2
CH
2
CH=CH
2 7.21 0 NO 2
CH
2
C-=OH
7.22 0 NO 2
CH
2 CH=CHCsHs 7.23 0 NO 2
CH
2
C=-CC
6
H
7.24 0 NO 2
SCH
3 7.25 0 NO 2 S0 2 Hs 7.26 0 NO 2 S-n-C 3
H-
7 7.27 0 NO 2 S-i-C 3
H
7 7.28 0 NO 2 S-n-C 4 HqI 7.29 0 NO 2 S-t-C 4 H9 7.30 0 NO 2 S-cyclo-0 3 7.31 0 NO 2
SCH
2
COHS
7.32 0 NO 2
SCH
2
C
6
H
4 -4-H 3 7.33 0 NO 2
SCH
2 C6H 4 -4-00H3 7.34 0 NO 2
SCH
2
C
6
H
4 -4-Cl 7.35 0 NO 2
SCH
2 CsH 4 -4-N0 2 7.36 0 NO 2
SCH
2 -2-furyl 7.37 0 NO 2
SCH
2 -2-thienyl 7.38 0 NO 2
SC
6 Hs 7.39 0 NO 2
SC
6
H
4 -4-CH 3 7.40 0 NO 2
SC
6
H
4 -4-00H 3 7.41 0 NO 2 SC6H 4 -4-Cl 7.42 0 NO 2
SC
6
H
4 -4-N0 2 7.43 0 NO 2
SCH
2
CH=-CH
2 7.44 0 NO 2
SCH
2
C=-CH
7.45 0 NO 2
SCH
2
CH=CHC
6 Hs 7.46 0 NO 2
SCH
2
CE=CC
6 Hs 7.47 0 NO 2 7.48 1 NO 2
OH
3 7.49 1 NO 2
C
2
H
7.50 1 NO 2 n-0 3
H
7 7.51 1 NO 2 i-C 3
H
7 7.52 1 NO 2 n-C 4 H9 7.53 1 NO 2 t-C 4
H
9 7.54 1 NO 2 cyclo-C 3
H
7.55 1 NO 2
CH
2
C
6
HS
7.56 1 NO 2
CH
2
C
6
H
4 -4-0H 3 76 7.57 1 NO 2
CH
2
C
6
H
4 -4-00H 3 7.58 1 NO 2
CH
2
COH
4 -4-CI 7.59 1 NO 2
CH
2 0 6
H
4 -4-N0 2 7.60 1 NO 2
CH
2 -2-furyt 7.61 1 NO 2 CHr22thioll 7.62 1 NO 2 CsH 7.63 1 NO 2
C
6
H
4 -4-0H 3 7.64 1 NO 2
C
6
H
4 -4-OCH 3 7.65 1 NO 2
C
6
H
4 -4-OI 7.66 1 NO 2
C
6
H
4 -4-N0 2 7.67 1 NO 2
CH
2 CH=0CH 2 7.68 1 NO 2
CH
2
C.-CH
7.69 1 NO 2
CH
2
CH=OCHC
6 Hs 7.70 1 NO 2
CH
2 C-=CCeHs 7.71 2 NO 2
CH
3 7.72 2 NO 2
C
2
H
7.73 2 NO 2 n-C 3
H
7 7.74 2 NO 2 i-C 3 Hy 7.75 2 NO 2 n-C 4
H
9 7.76 2 NO 2 t-C 4
H
9 7.77. 2 NO 2
CYCIO-C
3 Hs 7.78 2 NO 2 CHACHs 7.79 2 NO 2
CH
2
C
6
H
4 -4-CH 3 7.80 2 NO 2 0H 2 CsH 4 -4-OCH 3 7.81 2 NO 2
CH
2
C
6
H
4 -4-CI 7.82 2 NO 2
CH
2
C
6
H
4 -4-N0 2 7.83 2 NO 2 0H 2 -2-furyl 7.84 2 NO 2
CH
2 -2-thienyl 7.85 2 NO 2
CAH
7.86 2 NO 2
C
6
H
4 -4-CH 3 7.87 2 NO 2
C
6
H
4 -4-00H 3 7.88 2 NO 2 CeH 4 -4-CI 7.89 2 NO 2
C
6
H
4 -4-NO 2 -77- 7.90 2 NO 2
CH
2 CH=0CH 2 7.91 2 NO 2
CH
2
C-=CH
7.92 2 NO 2
CH
2 CH=-CHCeH 7.93 2 NO 2
CH
2 CE-CC6H 7.94 0 NO 2
CH
2
SCH
3 7.95 0 NO 2
CH
2
SC
2
H
7.96 0 NO 2
CH
2 S-n-C 3
H
7 7.97 0 NO 2
CH
2 S-i-C 3
H
7 7.98 0 NO 2
CH
2 S-n-C 4
H
9 7.99 0 NO 2
CH
2 S-t-C 4 H9 7.100 0 NO 2
CH
2 S-CYClO-C 3
H
7.101 0 NO 2
CH
2
SCH
2 7.102 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CH 3 7.103 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-OCH 3 7.104 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-CI 7.105 0 NO 2
CH
2
SCH
2 CcH 4 -4-N0 2 7.106 0 NO 2
CH
2 SCH2-2-furyI 7.107 0 NO 2
CH
2
SCH
2 -2-thienyt 7.108 0 NO 2
CH
2
SC
6 7.109 0 NO 2
CH
2
SC
6
H
4 -4-0H 3 7.110 0 NO 2
CH
2
SC
6
H
4 -4-OCH 3 7.111. 0 NO 2
CH
2
SC
6
H
4 -4-CI 7.112 0 NO 2
CH
2
SC
6
H
4 -4-N0 2 7.113 0 NO 2
CH
2
SCH
2 CH=0-H 2 7.114 0 NO 2
CH
2
SCH
2
C-=CH
7.115 0 NO 2
CH
2
SCH
2
CH=-CHC
6 Hs 7.116 0 NO 2
CH
2
SCH
2
C=-OC
6 Hs 7.117 0 NO 2
CH
2 7.118 0 CN CH 3 7.119 0 ON CAH -78 7.120 7.121 7.122 7.123.
7.124 7.125 7.126 7.127 7.128 7.129 7.130 7.131 7.132 7.133 7.134 7.135.
7.136 7.137 7.138 7.139 7.140 7.141 7.142 7.143 7.144 7.145 7.146 7.147 7.148 7.149 7.150 7.15 1 7.152 0 ON o CN 0 ON 0 ON 0 ON o ON 0 ON o ON o ON o ON 0 ON 0 ON o ON 0 ON o ON o ON 0 CN 0 ON 0 ON 0 ON 0 CN 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON 0 ON o ON 0 ON o ON 0 ON 0 ON n-C 3
H
7 i-0 3
H
7 n-0 4
H
9 t-C 4 H9
CYCIO-C
3 Hs
CH
2
O
5
H
CH
2 0 6
H
4 -4-CH 3
CH
2
C
8
H
4 -4-OCH3
CH
2 CeH 4 -4-OI 0H 2 CsH 4 -4-N02
CH
2 -2-furyl
CH
2 -2-thienyl
C
6
H
0 6
H
4 -4-CH 3
C
6
H
4 -4-00H 3
C
6
H
4 -4-CI
C
6
H
4 -4-N0 2
OH
2 CH=0CH 2
CH
2
O-=OH
CH
2 CH=0CHC 6 Hs
CH
2
CEOCC
6
SCH
3
SC
2
H
S-n-C 3
H
7 S-i-0 3
H
7 S-n-C4Hq S-t- 4
H
9 S-CYCIO-C3Hs
SCH
2
C
6 Hs
SCH
2
C
6
H
4 -4-CH 3
SCH
2
C
6
H
4 -4-00H 3
SCH
2
O
6 H4-4-CI
SCH
2
C
6
H
4 -4-N0 2 -79- 7.153 0 CN SCH 2 -2-furyl 7.154 0 ON SCHr22hielyt 7.155 0 ON SC 6 Hs 7.156 0 ON S0 6
H
4 -4-CH 3 7.157 0 ON SC 6
H
4 -4-00H 3 7.158 0 ON SC 6
H
4 -4-Ot 7.159 0 ON SC 6
H
4 -4-N0 2 7.160 0 ON SOH 2 OH=0CH 2 7.161 0 ON SCH 2
O=-CH
7.162 0 ON SOH 2 OH=OCHC6Hs 7.163 0 ON SCH 2 O-=G~sHs 7.164 0 ON 7.165 1 ON OH 3 7.166 1 ON 0 2 Hs 7.167 1 ON n-0 3
H
7 7.168 1 ON i-0 3 Hj 7.169 1 ON n-0 4
H
9 7.170 1 ON t-0 4
H
9 7.171 1 ON CYClO-0 3
H
7.172 1 ON 0H 2 0 6 Hs 7.173 1 ON 0H 2 0 6
H
4 -4-0H 3 7.174 1 ON 0H 2 0 6
H
4 -4-OCH 3 7.175 1 ON 0H 2 0 6
H
4 -4-CI 7.176 1 ON 0H 2 0 6
H
4 -4-N0 2 7.177 1 ON 0H 2 -2-furyl 7.178 1 ON 0H 2 -2-thienyl 7.179 1 ON CAH 7.180 1 ON 0 6
H
4 -4-CH 3 7.181 1 ON 0 6
H
4 -4-O0H 3 7.182 1 ON 0 6
H
4 -4-OI 7.183 7.184 7.185 7.186 7.187 7.188 7.189 7.190 7.191 7.192 7.193 7.194 7.195 7.196 7.197 7.198 7.199 7.200 7.201 7.202 7.203 7.204 7.205 7.206 7.207 7.208 7.209 7.210 7.2 11 7.212 7.2 13 7.214 7.215 1 CN 1 ON 1 ON I ON 1 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 ON 2 CN 2 ON 2 ON 2 ON 2 ON 2 ON o ON o ON o ON o ON o ON Cr 8
H
4 -4-N0 2
CH
2 CH=0CH 2
CH
2
O-=OH
CH
2 CH=OCHCeHs
CH
2
CO-CC
6
H
OH
3
C
2
H
n-C 3 H7 i-C 3
H
7 n-0 4 Hq t-C 4
H
9 cyciO-0 3
H
CH
2
C
6 Hs
CH
2
C
6
H
4 -4-CH 3
CH
2 CeH 4 -4-OCH 3
CH
2
C
6
H
4 -4-CI 0H 2 0 6
H
4 -4-N0 2
CH
2 -2-furyl 0H 2 -2-thienyl
CAH
C
6
H
4 -4-CH 3
CGH
4 -4-OCH 3
C
6
H
4 -4-Ct
C
6
H
4 -4-N0 2
OH
2 OH=0H 2
CH
2
OH
2 OH=CH0 6
H
5 s
CH
2 C=-CC6H
OH
2
SCH
3
OH
2
SC
2
H
OH
2 S-n-C 3
H
7
CH
2 S-i-C 3
H
7
CH
2 S-n-C 4 Hg -81- 7.216 0 ON OH 2 S-t-0 4 Hq 7.217 0 ON CH 2 S-cycIo-C3H 7.218 0 ON CH 2
SCH
2 CeH 7.219 0 ON OH 2
SOH
2
C.H
4 -4-0H 3 7.220 0 ON OH 2
SCH
2 CsH 4 -4-00H 3 7.221 0 ON OH 2
SOH
2 CH4Cl 7.222 0 ON OH 2
SOH
2
C
6 H4NO2 7.223 0 ON CH 2
SOH
2 -2-furyl 7.224 0 ON* CH 2 SCH22hienyl 7.225 0 ON 0H 2 S0 6
H
7.226 0 CN 0H- 2 S0 6
H-
4 -4-CH 3 7.227 0 CN CH 2
SC
6
H
4 -4-00H 3 7.228 0 CN CH 2
SO
6
H
4 -4-Ol 7.229 0 CN OH 2
SC
6
H
4 -4-N0 2 7.230 0 CN CH 2
SOH
2 OH=0CH 2 7.231 0 CN OH 2
SCH
2
CO=OH
7.232 0 CN CH 2
SOH
2
CH=CHC
6
H
7.233 0 ON CH 2
SOH
2 7.234 0 CN CH 2
C
NQ
Table 8 (O)n y Compound No. n X Y Z R 6 Physical data 8.1 0 N NO 2 NH i-C 3
H
7 8.2 0 N NO 2 NH OH 3 8.3 0 N NO 2 NH CH 2 C0 2 2
H
82- 8.4 8.6 8.7 8.8 8.9 8.10 8.11 8.12 8.13 8.14 8.15 8.16 8.17 8.18 8.19 8.20 8.21 8.22 8.23 8.24, 8.25 8.26 8.27 8.28 8.29 8.30 8.31 8.32 8.33 8.34 8.35 8.36 O N O N 0ON O N O N O N O N O N O N O N O N 1iN 1iN 2 N 2 N O N 0ON O N O N 0ON O N O N O N O N O N O N O N O N O N 1iN 1iN 2 N 2 N
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
ON NH ON NH CN NH CN NH CN NH ON NH CN NH CN NH ON NH ON NH ON NH ON NH CN NH ON NH CN NH ON NH ON NH CN NH
OH
2
C
6 Hs
CH
2 0 6
H
4 -4-CI 0-H CeH 4 -4-CI
CH
2 CH--0H 2
CH
2
C=-CH
SCH
3
SC
2
H
S-n-C 3
H
7 S-i- 3
H
7
SCH
2
C
6
H
i-03H 7
CH
2
CBHS
i-C 3
H
7
CH
2
C
6
HS
i-C 3
H
7 CH3
CH
2 C0 2
C
2
H
CH
2 0H 2
C
6
H
4 -4-CI
CAH
C
6
H
4 -4-CI
CH
2 CH=0H 2
CH
2
C-=OH
SCH
3
SC
2
H
S-n-0 3
H
7 S-i-C 3
H
7
SCH
2
C
6
H
i-C 3
H
7
CH
2 0 6 Hs i-C 3
H
7
CH
2
C
6 Hs 83 8.37 8.38 8.39 8.40 8.41 8.42 8.43 8.44 8.45 8.46 8.47 8.48 8.49 8.50 8.51 8.52 8.53 8.54 8.55 8.56 8.57 8.58 8.59 8.60 8.61 8.62 8.63 8.64 8.65 8.66 8.67 8.68 8.69 0 OH 0 OH 0 OH 0 OH 0 OH O OH 0 OH 0 OH o OH 0 OH o OH 0 OH 0 OH 0 OH 1 OH 1 OH 2 CH 2 OH O N O N O N O N O N O N O N O N O N O N O N O N O N O N 1 N
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
NO
2
NH
N0 2
NH
NO
2
NH
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3
NO
2
N-OH
3 i-0 3 H-i
OH
3
CH
2 C0 2 0 2 Hs
CH
2 C.Hs 0H 2 0 6 H4-4-CI 0 6
H
CeH 4 -4-CI
OH
2 CH=0H 2
CH
2
O-=OH
SOH
3
SC
2
H
S-n- 3
H
7 S-i-C 3
H
7
SCH
2 6 Hs i-C 3
H
7
CH
2
C
6
H
i-C 3
H
7
CH
2
C
6
,H
i-C 3
H
7
OH
3 0H 2 C0 2 2
H
CH
2
C
6
H
0H 2
C
6
H-
4 -4-OI
C
6
H
C
6
H
4 -4-OI
OH
2
CH=OCH
2
CH
2
O=-OH
SOH
3
SC
2 Hs S-n- 3
H
7 S-i-C 3
H
7
SCH
2 6
H
i-C 3
H
7 -84- 8.70 1 N NO 2
N-CH
3 0HA0H 8.71 2 N NO 2
N-OH
3 i-0 3
H
7 8.72 2 N NO 2
N-CH
3 0H 2
C
6
H
8.73 0 N ON N-OH 3 i-0 3
H
7 8.74 0 N ON N-OH 3
OH
3 8.75 0 N ON N-OH 3
CH
2 00O 2 2Hs 8.76 0 N CN N-OH 3 0H 2 0 6 Hs 8.77 0 N ON N-OH 3 0H 2 0 6
H
4 -4-CI 8.78 0 N ON N-OH 3 0 6 Hs 8.79 0 N ON N-OH 3 0 6
H
4 -4-OI 8.80 0 N ON N-OH 3
OH
2 OH--0H 2 8.81 0 N ON N-OH 3
CH
2
C=-OH
8.82 0 N ON N-OH 3
SOH
3 8.83 0 N ON N-OH 3 S0 2 Hs 8.84 0 N ON N-OH 3 S-n-0 3
H
7 8.85 0 N CN N-OH 3 S-i-0 3
H
7 8.86 0 N ON N-OH 3 S0H 2 0 8
H
8.87 1 N ON N-OH 3 i-0 3
H
7 8.88 1 N ON N-OH 3 0H 2 0 6
H
8.89 2 N ON N-OH 3 i-0 3
H
7 8.90. 2 N ON N-OH 3 0H 2 0 6 Hs 8.91 0 OH NO 2
N-OH
3 i-0 3
H
7 8.92 0 OH N0 2
N-OH
3
OH
3 8.93 0 OH NO 2
N-OH
3
CH
2 C0 2
C
2
H
8.94 0 OH NO 2
N-OH
3 0H 2 0 6
H
8.95 0 OH NO 2 N-OH.f. CH 2
O.H
4 -4-Ot 8.96 0 OH NO 2
N-OH
3
CAH
8.97 0 OH NO 2
N-OH
3 CrH 4 -4-OI 8.98 0 OH NO 2
N-OH
3
CH
2 CH=0H 2 8.99 0 OH NO 2
N-OH
3
CH
2
O=-CH
8.100 0 OH NO 2
N-OH
3
SOH
3 8.101 0 OH NO 2
N-OH
3 S0 2 Hs 8.102 0 OH NO 2
N-OH
3 S-n-0 3
H
7 8.103 0 OH NO 2
N-OH
3 S-i-0 3
H
7 8.104 0 CH NO 2
N-OH
3
SCH
2 CsHs 8.105 1 OH NO 2
N-OH
3 i-03117 8.106 1 OH NO 2
N-OH
3 0H 2
CGHIS
8.107 2 CH NO 2
N-OH
3 i-03117 8.108 2 OH NO 2
N-OH
3
CH
2 C.Hs 8.109 0 N NO 2
OH
2 i-C 3
H
7 8.110 0 N NO 2
OH
2
OH
3 8.111 0 N NO 2
CH
2
CH
2 00 2 0 2 Hs 8.112 0 N NO 2
OH
2 0HA0Hs 8.113 0 N NO 2
OH
2 0112C0614-4-01 8.114 0 N NO 2
OH
2 8.115 0 N NO 2
OH
2 C6H-4-4-C1 8.116 0 N NO 2
OH
2
CH
2 011=CH 2 8.117 0 N NO 2
OH
2
CH
2
CO-OH
8.118 0 N NO 2
OH
2
SCH
3 8.119 0 N N0 2
CH-
2
SC
2
H
8.120 0 N NO 2
OH
2 S-n-C 3
H
7 8.121 0 N NO 2
OH
2 S+0 3
H
7 8.122 0 N NO 2
OH
2 S011 2 0 6 11 8.123 1 N NO 2
OH
2 i-0 3
H
7 8.124 1 N NO 2
OH
2 0HA0Hs 8.125 2 N NO 2 0112 i-C 3
H
7 8.126 2 N NO 2 0112 0H 2 0 6
H
8.127 0 N ON OH 2 i-C 3
H
7 8.128 0 N ON OH 2
OH
3 8.129 0 N ON 0112 01120020215 8.130 0 N ON OH 2 011206115 8.131 0 N ON OH 2 01120614-4-Cl 8.132 0 N ON OH 2 C6Hs 8.133 0 N ON 0112 0614-4-01 8.134 0 N ON 0112 0112011=02 8.135 0 N ON 0112 CH2O-OH 86- 8.136 0 N ON OH 2
SCH
3 8.137 0 N CN OH 2
SC
2
H
8.138 0 N ON OH 2 S-n-C 3
H
7 8.139 0 N ON OH 2 S-i-C 3
H
7 8.140 0 N ON OH 2
SCH
2 CeHs 8.141 1 N ON OH 2 i-C 3
H
7 8.142 1 N ON OH 2 0HA0H 8.143 2 N ON OH 2 i-C 3
H
7 8.144 2 N ON OH 2
CH
2 0 6
H
8.145 0 OH NO 2
OH
2 i-0 3
H
7 8.146 0 OH NO 2
OH
2
OH
3 8.147 0 OH NO 2
OH
2
CH
2 C0 2 0 2 Hs 8.148 0 OH NO 2
OH
2
CH
2 0 6 Hs 8.149 0 OH NO 2
OH
2
CH
2
C
6
H
4 -4-CI 8.150 0 OH N0 2
OH
2
CAH
8.151 0 OH NO 2
OH
2
C
6
H
4 -4-CI 8.152 0 OH N0 2
CH
2
CH
2 CH=0CH 2 8.153 0 OH NO 2
OH
2
CH
2
C=-OH
8.154 0 OH NO 2
OH
2
SCH
3 8.155 0 OH NO 2
OH
2
SC
2 Hs 8.156 0 OH NO 2
OH
2 S-n-C 3
H
7 8.157 0 OH NO 2
OH
2 S-i-C 3
H
7 8.158 0 OH NO 2
OH
2
SCH
2
C
6 Hs 8.159 1 OH NO 2
OH
2 i-C 3
H
7 8.160 1 OH NO 2
OH
2 0H 2
C
6
H
8.161 2 OH NO 2
OH
2 i-C 3
H
7 8.162 2 OH NO 2
OH
2
CH
2
C
6 Hs 8.163 0 N NO 2 S i-C 3
H
7 8.164 0 N NO 2 S OH 3 8.165 0 N NO 2 S CH 2 C0 2 0 2
H
8.166 0 N NO 2 S CH 2
C
6
H
8.167 0 N NO 2 S CH 2
C
6
H
4 -4-CI 8.168 0 N NO 2 S CAH 87- 8.169 0 N NO 2 S C 6
H
4 -4-CI 8.170 0 N NO 2 S CH 2 OH--0H 2 8.171 0 N NO 2 S CH 2 OsOCH 8.172 0 N NO 2 S SCH 3 8.173 0 N NO 2 S SC 2 Hs 8.174 0 N NO 2 S S-n-C 3
H
7 8.175 0 N NO 2 S S-i-0 3
H
7 8.176 0 N NO 2 S SCH 2 CrHs 8.177 1 N NO 2 S i-0 3
H
7 8.178 1 N NO 2 S OH 2
C
6 Hs 8.179 2 N NO 2 S i-C 3
H
7 8.180 2 N NO 2 S 0H 2
C
6
H
8.181 0 N ON S i-C 3
H
7 8.182 0 N ON S OH 3 8.183 0 N ON S 0H 2 00 2 2 Hs 8.184 0 N ON S OH 2
C
6 Hs 8.185 0 N CN S 0H 2
COH
4 -4-CI 8.186 0 N ON S CsHs 8.187 0 N CN S CsH 4 -4-OI 8.188 0 N CN S OH 2
CH=CH
2 8.189 0 N ON S CH 2
O-=CH
8.190 0 N ON S SCH 3 8.191 0 N ON S SC 2 Hs 8.192 0 N ON S S-n-0 3
H
7 8.193 0 N ON S S-i-%3H 7 8.194 0 N ON S SCH 2
C
6 Hs 8.195 1 N ON S i-C 3
H
7 8.196 1 N ON S 0H 2
C
6 Hs 8.197 2 N ON S i-C 3
H
7 8.198 2 N ON S CH 2
C
6
H
8.199 0 OH NO 2 S i-C 3
H
7 8.200 0 OH NO 2 S OH 3 8.201 0 OH NO 2 S 0H 2 C0 2
C
2 Hs -88 8.202 8.203 8.204 8.205 8.206 8.207 8.208 8.209 8.210 8.211 8.212 8.213 8.214 8.215 8.216
CH
CH
CH
CH
OH
CH
CH
OH
OH
CH
OH
OH
CH
CH
CH
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2 N0 2
CH
2
C
6 Hs 0H 2
C
6
H
4 -"lC CsHs CsH 4 -4-Ol
CH
2 CH=0-H 2
CH
2
C=-CH
SCH
3
SC
2 Hs S-n-0 3
H-
7 S-i-C 3
H-
7
SCH
2 CeHs i-C 3
H
7
CH
2 0 6 Hs i-C 3
H
7 0H 2
C
6
H
Table 9 (O)n X
S
Ri
R
2 Compound n X Y Z R R 2 R6 Physical No. data 9.1 0 N 9.2 0 N 9.3 0 N 9.4 0 N 0 N 9.6 0 N 9.7 1 N 9.8 1 N 9.9 2 N
NO
2
N-OH
3
CH
3
NO
2
N-OH
3
OH
3
NO
2
N-OH
3
OH
3
NO
2
N-OH
3
CH
3
NO
2
N-OH
3
OH
3
NO
2
N-OH
3
OH
3
NO
2
N-CH
3 O H 3
NO
2
N-OH
3
OH
3
NO
2
N-OH
3
OH
3 H i-C 3
H-
7 H OH 3 H CH 2 C0 2 0 2
H
H 0H 2
C
6 Hs H 0e 6 H OH 2
CH=CH
2 H CeHs H CH 2 0 6 Hs H C 6 1- -89 9.10 9.11 9.12 9.13 9.14 9.15 9.16 9.17 9.18 9.19 9.20 9.21 9.22 9.23 9.24 9.25 9.26 9.27 9.28 9.29 9.30 9.31 9.32 9.33 9.34 9.35 9.36 9.37 9.38 9.39 9.40 9.41 9.42 2 N O N O N O N O N O N O N 1iN I N 2 N 2 N O CH 0 OH O OH O OH o OH 0 OH 1 OH 1 OH 2 OH 2 OH O N O N O N O N O N O N 1 N 1 N 2 N 2 N O N O N N0 2
ON
ON
ON
ON
ON
ON
ON
CN
ON
ON
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
ON
ON
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
CH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-CH
3
OH
3
N-OH
3 0 2 Hs
N-OH
3
CAH
N-OH
3 0 2
H
5
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2
H
5
N-OH
3 0 2 Hs
N-OH
3 0 2
H
5
N-OH
3 0 2 Hs
N-OH
3
CAH
N-OH
3
CAH
CH
2 0 6 Hs i-0 3
H
7
OH
3 0H 2 C0 2 2
H
0HA0Hs
CAH
OH
2
CH--CH
2
CAH
CHAN
6
H
0 6
H
CHAN
6
H
i-0 3
H
7
OH
3 0H 2 00 2 0 2 Hs 0HA0Hs
CAH
CH
2
CH=CH
2 0 6
H
CH
2 0 6
H
CAH
CHAN
6
H
i-C 3
H
7
OH
3
CH
2 C0 2 2 Hs
CH
2
C
6 Hs 0 6
H
OH
2
OH--CH
2 0 8
H
CH
2 0 6 Hs
CAH
0H 2 0 6
H
i-C 3
H
7
OH
3 9.43 9.44 9.45 9.46 9.47 9.48 9.49 9.50 9.51 9.52 9.53 9.54 9.55 9.56 9.57 9.58 9.59 9.60 9.61 9.62 9.63 9.64 9.65 9.66 9.67 9.68 9.69 9.70 9.71 9.72 9.73 9.74 9.75 O N O N O N O N 1iN 1 N 2 N 2 N O CH O OH O CH O OH O OH O OH 1 OH 1 OH 2 CH 2 OH O N O N O N O N O N O N 1 N 1 N 2 N 2 N O N O N
ON
CN
ON
ON
ON
CN
ON
ON
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
ON
ON
ON
ON
ON
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3
CAH
N-OH
3
CAH
N-OH
3 0 2
H
5
N-OH
3
CAH
N-OH
3
CAH
N-OH
3
CAH
N-OH
3
CAH
N-OH
3
CAH
N-OH
3 0 2 Hs
N-OH
3
CAH
N-OH
3
CAH
N-OH
3
CAH
N-OH
3
C
2 Hs
N-OH
3
C
2 Hs
N-CH
3
C
2 Hs
N-OH
3
CAH
N-OH
3
H
N-CH
3
H
N-OH
3
H
N-CH
3
H
N-OH
3
H
N-OH
3
H
N-CH
3
H
N-CH
3
H
N-OH
3
H
N-CH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
CH
2 00 2 0 2 Hs
CHAN.H
CAH
OH
2
CH--CH
2
C
6 Hs
CHAN
6
H
CAH
0H 2
C
6
H
i-C 3
H
7
OH
3 0H 2 00 2 0 2 Hs
CH
2 0 6
H
C
6 Hs
OH
2
CH=CH
2 O.Hs
CH
2 0 6 Hs CeH 5
CH
2 0 6 Hs i-0 3
H
7
OH
3 0H 2 00 2 2 Hs
CH
2 CsHs
O.HS
OH
2
OH---H
2
CAH
CH
2
C
6 Hs
O.H
5
CH
2 0 6 Hs i-0 3
H
7
OH
3
CH
2 C0 2 2 Hs
CH
2 0 6 Hs
CAH
O N O N O N -91- 9.76 9.77 9.78 9.79 9.80 9.81 9.82 9.83 9.84 9.85 9.86 9.87 9.88 9.89 9.90 9.91 9.92 9.93 9.94 9.95 9.96 9.97 9.98 9.99 9.100 9.101 9.102 9.103 9.104 9.105 9.106 9.107 9.108 O N 1iN 1iN 2 N 2 N 0 OH 0 OH 0 OH 0 OH 0 OH 0 OH 1 OH 1 OH 2 OH 2 OH O N O N O N O N O N O N 1iN 1iN 2 N 2 N O N O N O N O N O N O N 1iN I N
ON
ON
ON
ON
ON
N0 2 N0 2
NO
2
NO
2
NO
2 N0 2
NO
2 N0 2 N0 2 N0 2
NO
2 N0 2 N0 2 N0 2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
ON
ON
ON
ON
ON
ON
ON
ON
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
H
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
OH
3
CH
2 CH=0CH 2 CeHs 0H 2
C
6
H
CaHs CHANs~ i-0 3
H
7
OH
3
CH
2 C0 2 0 2
H
CH
2 CeHs
CAH
CH
2 CH=0CH 2
CAH
CHN
CSH
CH
2
C
6
H
i-C 3
H
7
CH
3 0H 2 00 2 0H
CHAN
6
H
CaHs
OH
2
CH--CH
2 CaHs 0H 2
C
6
H
0 6 Hs
CH
2 CsHs i-C 3
H
7
OH
3 0H 2 C0 2 0 2 Hs
CH
2
C
6 Hs
CAH
CH
2
CH=CH
2 0 6 Hs
CH
2 CsHs -92- 9.109 9.110 9.111 9.112 9.113 9.114 9.115 9.116 9.117 9.118 9.119 9.120 9.121 9.122 9.123 9.124 9.125 9.126 9.127 9.128 9.1219 9.130 9.131 9.132 9.133 9.134 9.135 9.136 9.137 9.138 9.139 9.140 9.141 2 N 2 N 0 OH 0 OH 0 CH 0 OH 0 OH 0 OH 1 OH 1 OH 2 OH 2 OH O N O N O N O N 0ON O N 1 N 1 N 2 N 2 N O N O N O N O N O N O N 1 N 1 N 2 N 2 N 0 OH
ON
CN
NO
2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
NO
2
NO
2
ON
ON
ON
ON
ON
ON
ON
ON
ON
ON
NO
2
N-OH
3
OH
3
N-OH
3
CH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-OH
3
OH
3
N-CH
3
OH
3
N-OH
3
OH
3
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-CH
3 0 2
H
5
N-OH
3 %2H 5
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2
H
5
N-OH
3 0 2
H
5
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3 0 2 Hs
N-OH
3
CAH
N-OH
3 0 2 Hs
N-OH
3 0 2
H
5
N-OH
3
CAH
N-OH
3 0 2
H
5
N-OH
3
C
2 Hs
OH
3 0 6
H
OH
3 0H 2 0 6 Hs
OH
3 i-0, 3
H
7
OH
3
OH
3
OH
3 0H 2 00 2 0 2
H
OH
3
CH
2 0 6 Hs
OH
3 CsHs
OH
3
OH
2 OH=0H 2
OH
3 0 6
H
OH
3 0H 2 0 6
H
OH
3
CAH
OH
3 0H 2 0 6
H
OH
3 i-0 3
H
7
OH
3
OH
3
OH
3 0H 2 00 2 0 2 Hs
OH
3 0H 2 0 6 Hs
OH
3 0 6
H
OH
3
OH
2 OH=0H 2
OH
3 0 6 Hs
OH
3 0H 2 0 6 Hs
OH
3 0 6 Hs
OH
3 0HA0H
OH
3 i-0 3
H
7
OH
3
OH
3
OH
3 0H 2 00 2 0 2
H
OH
3 0H 2 0 6 Hs
OH
3 0 6 Hs
OH
3
OH
2 OH--0H 2
OH
3
CAH
OH
3 0H 2 0 6 Hs
OH
3
CAH
OH
3 0H 2 0 6 Hs
OH
3 i-C 3
H
7 93- 9.142 0 OH NO 2
N-CH
3
C
2
H
5
OH
3
OH
3 9.143 0 OH NO 2
N-OH
3 0 2 Hs CH 3
CH
2 C0 2 2 Hs 9.144 0 OH NO 2
N-OH
3
C
2 Hs OH 3
CH
2
C
6 Hs 9.145 0 OH NO 2
N-OH
3 CAH OH 3
O.H
9.146 0 OH NO 2
N-OH
3 0 2 Hs OH 3
OH
2 OH=0CH 2 9.147 1 OH NO 2
N-OH
3 0 2
H
5
OH
3 CeH 9.148 1 OH NO 2
N-OH
3 0 2 Hs OH 3
CH
9.149 2 OH N0 2
N-OH
3
C
2 h OH 3 0 0
H
9.150 2 OH NO 2
N-OH
3
C
2 Hs OH 3
CH
2 CoHs 9.151 0 N NO 2
N-OH
3 H OH 3 i-C 3
H
7 9.152 0 N NO 2
N-OH
3 H OH 3
OH
3 9.153 0 N NO 2
N-OH
3 H OH 3 0H 2 00 2 0 2 Hs 9.154 0 N NO 2
N-OH
3 H OH 3 0H 2 0.Hs 9.155 0 N NO 2
N-OH
3 H OH 3 0 6
H
9.156 0 N NO 2
N-OH
3 H OH 3
CH
2 OH=0-H 2 9.157 1 N NO 2
N-OH
3 H OH 3 0 6 Hs 9.158 1 N NO 2
N-OH
3 H OH 3
OH
2 0 6 Hs 9.159 2 N NO 2
N-OH
3 H OH 3
CAH
9.160 2 N NO 2
N-OH
3 H OH 3 0H 2 0 6 Hs 9.161 0 N ON N-OH 3 H OH 3 i-0 3
H
7 9.162 0 N ON N-OH 3 H OH 3
CH
3 9.163 0 N ON N-OH 3 H OH 3 0H 2 C0 2
C
2 Hs 9.164 0 N ON N-OH 3 H OH 3 0H 2
C
6
H
9.165 0 N ON N-OH 3 H OH 3
CAH
9.166 0 N ON N-OH 3 H OH 3
OH
2 OH--0H 2 9.167 1 N ON N-OH 3 H OH 3
CAH
9.168 1 N ON N-OH 3 H OH 3 0H 2 0 6 Hs 9.169 2 N ON N-OH 3 H OH 3
CAH
9.170 2 N ON N-OH 3 H OH 3 0H 2 0 6
H
9.171 0 OH NO 2
N-OH
3 H OH 3 i-0 3
H
7 9.172 0 OH NO 2
N-OH
3 H OH 3
CH
3 9.173 0 OH NO 2
N-OH
3 H OH 3 0H 2 00 2 0 2 Hs 9.174 0 OH NO 2
N-OH
3 H OH 3
OH
2 OeHs 94 9.175 0 OH NO 2
N-OH
3 H OH 3 CeH 9.176 0 CH NO 2
N-OH
3 H OH 3
CH
2 CH=0CH 2 9.177 1 OH NO 2
N-OH
3 H CH 3 0 6 Hs 9.178 1 OH NO 2
N-OH
3 H OH 3
CH
2 CeH 9.179 2 CH NO 2
N-OH
3 H OH 3 CaHs 9.180 2 OH NO 2
N-OH
3 H OH 3
CH
2
C
6
H
9.181 0 N NO 2
OH
2
OH
3 H i-0 3
H
7 9.182 0 N NO 2
OH
2
OH
3 H OH 3 9.183 0 N NO 2
OH
2
OH
3 H 0H 2 0;0 2 0 2 Hs 9.184 0 N NO 2
OH
2
OH
3 H CH 2 0 5 Hs 9.185 0 N NO 2
OH
2
OH
3 H O.Hs 9.186 0 N NO 2
OH
2
OH
3 H OH 2
CH=CH
2 9.187 1 N NO 2
OH
2
OH
3 H CAH 9.188 1 N NO 2
OH
2
OH
3 H CH 2
C
6
H
9.189 2 N NO 2
OH
2
OH
3 H C 6 Hs 9.190 2 N NO 2
OH
2
OH
3 H 0HA0Hs 9.191 0 N ON OH 2
OH
3 H i-C 3
H
7 9.192 0 N ON OH 2
OH
3 H OH 3 9.193 0 N ON OH 2
OH
3 H CH 2 C0 2
C
2 Hs 9.194 0 N ON OH 2
OH
3 H 0HA0H 9.195 0 N ON OH 2
OH
3 H CAH 9.196, 0 N ON OH 2
OH
3 H OH 2 OH=0H 2 9.197 1 N ON OH 2
OH
3 H CeH 9.198 1 N ON OH 2
CH
3 H CH 2
C
6
H
9.199 2 N ON OH 2
OH
3 H C 6 Hs 9.200 2 N ON OH 2
OH
3 H CH 2 0 6 Hs 9.20 1 0 OH NO 2
OH
2
OH
3 H i-C 3
H
7 9.202 0 OH NO 2
OH
2
OH
3 H OH 3 9.203 0 OH NO 2
OH
2
OH
3 H CH 2 C0 2 0 2
H
9.204 0 OH NO 2
OH
2
OH
3 H CHA0Hs 9.205 0 OH NO 2
OH
2
OH
3 H CsHs 9.206 0 OH NO 2
OH
2
OH
3 H OH 2 OH=0H 2 9.207 1 CH NO 2
CH
2
OH
3 H CAH 95 9.208 9.209 9.210 9.211 9.212 9.213 9.214 9.215 9.216 9.217 9.218 9.219 9.220 9.22 1 9.222 9.223 9.224 9.225 9.226 9.227 9.228 9.229 9.230 9.231 9.232 9.233 9.234 9.235 9.236 9.237 9.238 9.239 9.240 1 CH 2 OH 2 OH O N O N O N O N O N O N 1iN 1iN 2 N 2 N O N O N O N o N O N O N 1iN 1iN 2 N 2 N 0 CH O CH O OH O CH O CH O OH 1 CH 1 OH 2 OH 2 CH
NO
2
NO
2
NO
2
NO
2 N0 2
NO
2
NO
2
NO
2
NO
2 N0 2 N0 2
NO
2
NO
2
ON
ON
ON
CN
ON
ON
CN
ON
ON
ON
N0 2 N0 2 N0 2 N0 2 N0 2 N0 2 N0 2
NO
2 N0 2 N0 2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
CH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2 0112
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
2
OH
3
H
OH
3
H
OH
3
H
0 2 Hs H
C
2
H
5
H
0 2
H
5
H
0 2
H
5
H
C
2
H
5
H
C
2 Hs H 0 2 Hs H 0 2
H
5
H
C
2
H
5
H
CAH H 0 2 Hs H 0 2
H
5
H
0 2
H
5
H
C
2 H, H 0 2
H
5
H
CAH H CAH H CAH H 0 2
H
5
H
CAH H CAH H CAH H CAH H CAH H 0 2 Hs H 0 2 Hs H CAH H CAH H 0 2 Hs H CAH H
CH
2 0 6
H
C
6
H
CH
2
C
6 Hs i-C 3
H
7
OH
3
CH
2 C0 2 0 2 Hs
CH
2
C
6 Hs
CH
2
CH=CH
2 0 6 Hs
CH
2
C
6
H
CAH
CH
2 0 6 Hs i-0 3
H
7
OH
3
CH
2 00 2 0 2 Hs
CH
2
C
6 Hs 0 6
H
CH
2
CH=CH
2 0 6 Hs 0H 2 0 6 Hs
C
6 Hs
CH
2 0 6 Hs i-0 3 H7
OH
3
CH
2 c0 2 2
H
0H 2
C
6 Hs
C
6 Hs
CH
2 OH=0H 2 0 6 Hs
CH
2 0 6
H
CAH
CH
2
C
6 Hs 96 9.241 0 N NO 2
OH
2 H H i-C 3
H
7 9.242 0 N NO 2
OH
2 H H OH 3 9.243 0 N NO 2
OH
2 H H CH 2 C0 2 0 2
H
9.244 0 N NO 2
OH
2 H H CH 9.245 0 N NO 2
OH
2 H H C 6 Hs 9.246 0 N NO 2
CH
2 H H OH 2 CH--0H 2 9.247 1 N NO 2
OH
2 H H CeHs 9.248 1 N NO 2
OH
2 H H CH 2 0 6 Hs 9.249 2 N NO 2
OH
2 H H CsHs 9.250 2 N NO 2
OH
2 H H OHAOH 9.251 0 N CN OH 2 H H i-C 3
H
7 9.252 0 N ON CH 2 H H CH 3 9.253 0 N ON OH 2 H H 0H 2 00 2 0 2
H
9.254 0 N ON OH 2 H H 0H 2 0 6 Hs 9.255 0 N ON OH 2 H H CAH 9.256 0 N ON OH 2 H H OH 2
CH--CH
2 9.257 1 N CN OH 2 H H 0 6
H
9.258 1 N ON OH 2 H H 0H 2
C
6
H
9.259 2 N ON OH 2 H H Ce 6 9.260 2 N ON OH 2 H H 0H 2
C
6 Hs 9.261 0 OH NO 2
OH
2 H H i-C3H 7 9.262 0 OH NO 2
OH
2 H H OH 3 9.263 0 OH NO 2
OH
2 H H CH 2 C0 2
C
2 Hs 9.264 0 OH NO 2
OH
2 H H CH 2 0 6 Hs 9.265 0 OH NO 2
OH
2 H H 0 6
H
9.266 0 OH NO 2
OH
2 H H OH 2 OH=0H 2 9.267 1 OH NO 2
OH
2 H H CAH 9.268 1 OH NO 2
OH
2 H H CH 2
C
6
H
9.269 2 OH NO 2
OH
2 H H CAH 9.270 2 OH NO 2
OH
2 H H 0H 2
C
6 Hs 97 Table (O)n
RJ
Compound No. n Y Re Physical data 10.1 0 NO 2
OH
3 10.2 0 NO 2 0 2 Hs 10.3 0 NO 2 n-C 3
H
7 10.4 0 NO 2 i-%3H 7 10.5 0 NO 2 n-C 4 H.1 10.6 0 NO 2 t-C 4 Hg1 10.7 0 NO 2 CYClo-C 3 Hs 10.8 0 NO 2
CH
2
C
6
H
10.9 0 NO 2
CH
2 CsH 4 -4-CH 3 10.10 0 NO 2
CH
2
C
6
H
4 -4-00H 3 10.11 0 NO 2
CH
2
C
6
H
4 -4-CI 10.12 0 NO 2
CH
2
C
6
H
4 -4-N0 2 10.13 0 NO 2
CH
2 -2-furyl 10.14 0 NO 2 0H 2 -2-thienyl 10.15 0 NO 2
C
6 1- 10.16 0 NO 2
C
6
H
4 -4-CH 3 10.17 0 NO 2
C
6
H-
4 -4-00H 3 10.18 0 NO 2
C
6
H
4 -4-CI 10.19 0 NO 2
C
6
H-
4 -4-N0 2 10.20 0 NO 2
CH
2
CH=CH
2 10.21 0 NO 2
CH
2
C-=CH
10.22 0 NO 2
CH
2
CH=-CHC
6
H
10.23 0 NO 2
CH
2 C-=CC6Hs 10.24 0 NO 2
SCH
3 10.25 0 NO 2
SCAH
10.26 0 NO 2 S-n-C 3
H
7 98 10.27 0 NO 2 S-i-C 3
H
7 10.28 0 NO 2 S-n-0 4 Hq 10.29 0 NO 2 S-t-C 4
H
9 10.30 0 NO 2 S..cYCIO-0 3
H
10.31 0 NO 2
SCH
2 C9Hs 10.32 0 NO 2
SCH
2 COH4-4-OH 3 10.33 0 NO 2
SCH
2 CsH 4 400H 3 10.34 0 NO 2
SCH
2 C"H-4-CI 10.35 0 NO 2
SCH
2
COH
4 -4-N0 2 10.36 0 NO 2
SCH
2 -2-furyl 10.37 0 NO 2
SCH
2 -2-thienyl 10.38 0 NO 2
SC
6 Hs 10.39 0 NO 2 SCcH 4 -4-0H 3 10.40 0 NO 2
SC
6
H
4 -4-OCH 3 10.41 0 NO 2
SC
6
H
4 -4-CI 10.42 0 NO 2
SC
6
H
4 -4-N0 2 10.43 0 NO 2
SCH
2 CH--0H 2 10.44 0 NO 2
SCH
2
C-=CH
10.45 0 NO 2
SCH
2
CH=CHC
6
H
10.46 0 NO 2
SCH
2
C-=CC
6 H6 10.47 0 NO 2 10.48 1 NO 2
CH
3 10.49 1 NO 2
C
2
H
10.50 1 NO 2 n-C 3
H
7 10.51 1 NO 2 i-C 3 H7 10.52 1 NO 2 n-C 4
H
9 10.53 1 NO 2 t-C 4
H
9 10.54 1 NO 2
CYCIO-C
3
H
10.55 1 NO 2
CH
2 C6Hs 10.56 1 NO 2
CH
2
C
6
H
4 -4-CH 3 -99 10.57 1 NO 2
CH
2 CsH 4 -4-OCH 3 10.58 1 NO 2
CH
2
C
6
H
4 -4-CI 10.59 1 NO 2
CH
2
C
6
H
4 -4-N0 2 10.60 1 NO 2
CH
2 -2-turyl 10.61 1 NO 2
CH
2 -2-thienyl 10.62 1 NO 2
C
6
H
10.63 1 NO 2
C
6
H
4 -4-0H 3 10.64 1 NO 2
C
6
H
4 -4-OCH 3 10.65 1 NO 2
C
6
H
4 -4-CI 10.66 1 NO 2 0 6
H
4 -4-NO 2 10.67 1 NO 2
CH
2
CH=CH
2 10.68 1 NO 2
CH
2
CE=CH
10.69 1 NO 2
CH
2
CH=CHC
6 Hs 10.70 1 NO 2
CH
2
C-=CC
6
H
10.71 2 NO 2
CH
3 10.72 2 NO 2
CAH
10.73 2 NO 2 n-C 3
H
7 10.74 2 NO 2 i-C 3
H
7 10.75 2 NO 2 n-C 4
H
9 10.76 2 NO 2 t-C 4 Hq 10.77 2 NO 2 CYClO-C 3 Hs 10.78 2 NO 2
CH
2
C
6
H
10.79 2 NO 2
CH
2
C
6
H
4 -4-CH 3 10.80 2 NO 2
CH
2
C
6
H
4 -4-OCH 3 10.81 2 NO 2
CH
2
C
6
H
4 -4-CI 10.82 2 NO 2
CH
2
C
6
H
4 -4-N0 2 10.83 2 NO 2
CH
2 -2-furyl 10.84 2 NO 2
CH
2 -2-thienyl 10.85 2 NO 2
CAH
10.86 2 NO 2
C
6
H
4 -4-CH 3 10.87 2 NO 2
C
6
H
4 -4-OCH 3 10.88 2 NO 2
C
6
H
4 -4-CI 10.89 2 NO 2
C
6
H
4 -4-N0 2 -100- 10.90 2 NO 2
CH
2 CH--0H 2 10.91 2 NO 2
CH
2
C-=CH
10.92 2 NO 2
CH
2 CH=-CHC6Hs 10.93 2 NO 2
CH
2 C=-CCeHs 10.94 0 NO 2
CH
2
SCH
3 10.95 0 NO 2
CH
2
SC
2 Hs 10.96 0 NO 2
CH
2 S-n-0 3
H
7 10.97 0 NO 2
CH
2 S-i-C 3
H
7 10.98 0 NO 2
CH
2 S-n-C 4 Hg 10.99 0 NO 2
CH
2 S-t-0 4
H
9 10.100 0 NO 2
CH
2 S-CYClo-C 3
H
10.101 0 NO 2
CH
2
SCH
2
C
6
H
10.102 0 NO 2
CH
2
SCH
2 CsH, 4 -4-CH 3 10.103 0 NO 2
CH
2
SCH
2 CsH 4 -4-OCH 3 10.104 0 NO 2
CH
2
SCH
2 COH4-4-CI 10.105 0 NO 2
CH
2
SCH
2
C
6
H
4 -4-N0 2 10.1 06 0 NO 2
CH
2
SCH
2 -2-furyl 10.107 0 NO 2
CH
2
SCH
2 -2-thienyl 10.1 08 0 NO 2
CH
2
SC
6
H
10.109 0 NO 2
CH
2
SC
6
H
4 -4-CH 3 10.110 0 NO 2
CH
2
SC
6
H
4 -4-OCH 3 10.111. 0 NO 2
CH
2 SCeH 4 -4-CI 10.112 0 NO 2
CH
2 SCsH 4 -4-N0 2 10.113 0 NO 2
CH
2
SCH
2
CH=CH
2 10.114 0 NO 2
CH
2
SCH
2
C-=CH
10.115 0 NO 2
CH
2
SCH
2
CH=-CHC
6
H
10.116 0 NO 2
CH
2
SCH
2
C-=CC
6
H
10.117 0 NO 2
H
10.118 0 ON CH 3 10.119 0 CN C 2
H
101 10.120 0 CN n-C 3
H
7 10.121 0 ON i-C 3
H
7 10.122 0 CN n-C 4
H
9 10.123 0 CN t-0 4
H
9 10.124 0 ON CYCIO-C 3 Hs 10.125 0 ON 0HA0H 10.126 0 CN OH 2
OH
4 -4-0H 3 10.1 27 0 ON 0H 2 0 6
H
4 -4-00H 3 10.128 0 CN 0H 2 0 6
H
4 -4-OI 10.129 0 CN CH 2
C
6
H
4 -4-N0 2 10.130 0 ON 0H 2 -2-furyi 10.131 0 ON 0H 2 -2-thienyl 10.132 0 ON 0 6
H
10.133 0 ON C 6
H
4 -4-CH 3 10.134 0 ON 0 6
H
4 -4-OOH 3 10.135 0 ON O 6
H
4 -4-OI 10.136 0 ON 0 6
H
4 -4-N0 2 10.137 0 ON OH 2 OH=0CH 2 10.138 0 ON CH 2
C-=-H
10.139 0 ON OH 2 OH=0CH0 6
H
10.1.40 0 ON CH 2
C-=CC
6 Hs 10.141 0 ON SOH 3 10.142 0 ON S0 2
H
10.143 0 ON S-n-0 3 H7 10.144 0 ON S-i-0 3
H
7 10.145 0 ON S-n-0 4 Hq 10.146 0 ON S-t-0 4
H
9 10.147 0 ON S-CYClO-0 3
H
10.148 0 ON S0H 2 0 6
H
10.149 0 ON S0H 2 0 6
H
4 -4-0H 3 10.150 0 ON S0H 2 0 6
H
4 -4-00H 3 10.151 0 ON S0H 2 0 6
H
4 -4-OI 10.152 0 ON SCH 2
C
6
H
4 -4-N0 2 -102 10.153 0 CN SCH2-2-fLuryI 10.154 0 ON SCH 2 -2-thienyl 10.155 0 ON S0 6 Hs 10.1 56 0 ON S0 6
H
4 -4-0H 3 10.157 0 ON SO 6
H
4 -4-00H 3 10.158 0 ON S0 6
H
4 -4-CI 10.159 0 ON S0 6
H
4 -4-N0 2 10.160 0 ON SCH 2 OH=0CH 2 10.161 0 ON SCH 2
O-=CH
10.162 0 ON SOH 2 OH=OHCrHs 10.163 0 CN SCH 2
OC-=C
6 Hs 10.164 0 ON 10.165 1 ON OH 3 10.166 1 ON 0 2 Hs 10.167 1 ON n-0 3 H7 10.168 1 ON i-0 3
H
7 10.169 1 ON n-0 4
H
9 10.170 1 ON t-0 4
H
9 10.171 1 ON CYCIO-0 3
H
10.172 1 ON 0H 2 0 6
H
10.173 1 CN 0H 2 0 6
H
4 -4-0H 3 10.174 1 ON CH 2
C
6
H
4 -4-00H 3 10.175 1 ON CH 2 0 6
H
4 -4-OI 10.176 1 ON 0H 2 0 6
H
4 -4-N0 2 10.177 1 ON 0H 2 -2-furyl 10.178 1 ON 0H 2 -2-thienyl 10.179 1 ON CAH 10.180 1 ON 0 6
H
4 -4-0H 3 10.181 1 ON 0 6
H
4 -4-00H 3 10.182 1 ON 0 6
H
4 -4-CI -103- 10.183 1 ON 0 6
H
4 -4-N0 2 10.184 1 CN CH 2
CH--OH
2 10.185 1 ON CH 2
O.OCH
10.186 1 ON CH 2 CH--0H0 6
H
10.187 1 ON OH 2 O=-OC.Hs 10.188 2 ON OH 3 10.189 2 ON 0 2 Hs 10.190 2 ON n-0 3
H
7 10.191 2 ON i-0 3
H
7 10.192 2 ON n-C 4 Hq 10.193 2 ON t-0 4
H
9 10.194 2 ON CYClO-0 3
H
10.195 2 ON CH 2 0 6 Hs 10.196 2 CN CH 2 0 6
;H
4 -4-0H 3 10.197 2 ON CH 2 0 6
H
4 -4-00H 3 10.198 2 ON 0H 2 0 6
H
4 -4-OI 10.199 2 ON CH 2 0 6
H
4 -4-N0 2 10.200 2 CN 0H 2 -2-furyl 10.201 2 ON CH 2 -2-thienyl 10.202 2 ON CAH 10.203 2 ON 0 6
H
4 -4-0H 3 10.204 2 CN 0 6
H
4 -4-00H 3 10.205 2 ON C 6
H
4 -4-OI 10.206 2 ON 0 6
H
4 -4-N0 2 10.207 2 ON OH 2 OH=0H 2 10.208 2 CN CH 2
CEOCH
10.209 2 ON OH 2
CH=OHO
6 Hs 10.210 2 ON CH 2 C-=CC6H 10.211 0 ON OH 2
SCH
3 10.212 0 ON CH 2 S0 2
H
10.213 0 ON OH 2 S-n-0 3
H
7 10.214 0 ON OH 2 S-i-0 3
H,
10.215 0 ON CH 2 S-n-C 4
H
9 -104 10.216 0 ON CH 2 S-t-C 4
H,
10.217 0 CN OH 2 S-cyclo-0 3 Hs 10.218 0 ON OH 2
SCH
2 CsH 10.219 0 ON OH 2
SCH
2 CeH 4 -4-CH3 10.220 0 ON OH 2
SCH
2 CeH 4 -4-OCH3 10.221 0 CN CH 2
SCH
2
C
6 H4-4-CI 10.222 0 CN 0H 2 S0H 2
COH
4 -4-N0 2 10.223 0 ON OH 2 SCH-2-turyI 10.224 0 ON OH 2 SOH2-2-thienyl 10.225 0 ON CH 2
SC
6 Hs 10.226 0 ON OH 2
SC
6
H
4 -4-0H 3 10.227 0 ON 0H 2
SC
6
H
4 -4-OCH 3 10.228 0 ON 0H 2 S0 6
H
4 -4-CI 10.229 0 ON OH 2
SO
6
H
4 -4-N0 2 10.230 0 ON OH 2
SOH
2 OH=0CH 2 10.231 0 ON CH 2
SOH
2
O=-CH
10.232 0 ON OH 2
SOH
2
OH=OHC
6 Hs 10.233 0 ON CH 2
SOH
2 O.00C 6 Hs 10.234 0 ON OH %2s N N rl I -105- Table 11 Compound No. Structural formula Physical data 11.1 NNO. 132-1350 a-i
CH
NON1 11.2 92-930 (0 11.3 11.4 11.5 11.6 Cl NN0 2
N
H
3
C
NON
N
H
3
C
CK(
11.7 11.7 NNO~ -106- 11.8 11.9 11.10 11.11 11.12 11.13 11.14 -107- Table 12 x-Y Cl
N
d^^vI,- Compound No. X Y Z Physical data 12.1 N NO 2
NH
12.2 N CN NH 12.3 CH NO 2
NH
12.4 N NO 2
N-CH
3 12.5 N CN N-CH 3 12.6 CH NO 2
N-CH
3 12.7 N NO 2
CH
2 12.8 N CN CH 2 12.9 CH NO 2
CH
2 12.10 N NOz S 12.11 N CN S 12.12 CH NO 2
S
Table 13 x-Y N
I
RI
R
2 Compound No. X Y Z R, R 2 Physical data 13.1 13.2 13.3 13.4 13.5 13.6 N NO 2
N-CH
3
CH
3
H
N CN N-CH 3
CH
3
H
CH NO 2
N-CH
3
CH
3
H
N NO 2
N-CH
3 CzH 5
H
N CN N-CH 3
C
2 Hs H CH NO 2
N-CH
3
C
2 Hs H -108- 00 13.7 N NO N-CH 3 H H S13.8 N CN N-CH3 H H 0o 13.9 CH NO, N-CH 2 H H 13.10 N NO, N-CH 3 CH CH3 13.11 N CN N-CHs CH3 CH 3 13.12 CH NO 2 N-CH3 CH3 CH3 O 13.13 N NOa N-CH3 CaHs CH 3 S13.14 N CN N-CH3 CaHs CH3 13.15 CH NO2 N-CH3 CaHs CH3 13.16 N NOa N-CH 3 H CH3 13.17 N. CN N-CH3 H CH 3 13.18 CH NOa N-CH3 H CH 3 13.19 N N02 CH CH3 H 13.20 N CN CH2 CH 3
H
13.21 CH NO. CH2 CH3 H 13.22 N NO. CH, CaH H 13.23 N CN CH, CaHs H 13.24 CH NOa CHa CaHs H 13.25 N NO. CH H H 13.26 N CN CH, H H 13.27 CH NO. CH, H H Throughout this specification and the'claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.
Claims (1)
109- THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS: 1. A process for preparing a compound of the formula IV: (O)n R, (IV), R6 N in the free form or the form of a salt, wherein R 6 is unsubstituted or R 8 -substituted alkyl, unsubstituted or R 8 -substituted alkenyl, unsubstituted or R 8 -substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl, SR 7 (alkylene)SH or (alkylene)SR 7 R 7 is unsubstituted or R 4 -substituted alkyl, unsubstituted or R 4 -substituted alkenyl, unsubstituted or R 4 -substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl or a group of the formula 12Y R1.AR2(II), \I NZ X is CH or N, Y is NO2 or CN, Z is CHR 3 O, NR 3 or S, R 1 and R 2 are either each, independently of the other, hydrogen or unsubstituted or R 4 -substituted alkyl or together a two- or three-membered alkylene bridge or a two- or three-membered alkylene bridge in which one member is replaced by a hetero member selected from the group, consisting of NR 5 O and S, R 3 is H or unsubstituted or R 4 -substituted alkyl, R 4 is an unsubstituted or substituted aryl or heteroaryl group, and R 5 is H or alkyl, P:\OPER\Kbm\2006200339 vol amnd doc.16A)2/06 -110- R 8 is an unsubstituted or substituted aryl or heteroaryl group, -COOH, COOM, wherein M is an alkali metal, or -COO-C1-Cs-alkyl, n is 0, 1 or 2, and X, is a leaving group; which comprises either reacting a compound of the formula S %Y (VI), which is known, with a compound of the formula R 6 X 2 in which R 6 has the meaning stated for the formula IV and X 2 is a leaving group, and subsequently reacting with a compound of the formula QX, in which Q is an acidic group and X 1 has the meaning stated for the formula IV, to give compounds of the formula IV in which n is 0 which can, if desired, be converted further to compounds of the formula IV in which n is 1 or 2 by using an oxidizing agent, or reacting a compound of the formula R6 S S N _(VII), NY wherein R 6 has the meaning given for formula IV, with a compound of the formula QX 1 wherein Q is an acidic group and X, has the meaning given for formula IV, in order to obtain a compound of the formula IV, wherein n is 0, and if desired further reacting the compound of the formula IV, wherein n is 0, with an oxidizing agent in order to obtain a compound of the formula IV, wherein n is 1 or 2. 2. A process according to claim 1 wherein Q is an inorganic acid group. 3. A process according to claim 2 wherein Q is SO 2 X 1 4. A process according to claim 1 wherein the oxidizing agent is hydrogen peroxide. P:\OPER\KbmU2006200339 vol amend doc-16/02/06 -111 A process for preparing a compound of the formula VII, as defined in claim 1, which comprises reacting a compound of the formula VI, as defined in claim 1, with a compound of the formula R 6 X 2 wherein Re has the meaning as given for formula IV and X 2 is a leaving group. 6. A process according to claim 5 wherein the reaction is carried out in the presence of a base. 7. A compound of the formula VII, as defined in claim 1. 8. A process according to claim 1 or claim 5, substantially as hereinbefore described and/or exemplified. 9. A compound of formula IV prepared by the process of any one of claims 1 to 4. A compound of formula VII prepared by the process of claim 5 or claim 6. DATED this 16 th day of February, 2006 Syngenta Participations AG By DAVIES COLLISON CAVE Patent Attorneys for the Applicants
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2006200339A AU2006200339B2 (en) | 1995-12-01 | 2006-01-25 | Process for preparing 2-chlorothiazole compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3412/95 | 1995-12-01 | ||
| AU2002300672A AU2002300672B2 (en) | 1995-12-01 | 2002-08-21 | Process for preparing 2-chlorothiazole compounds |
| AU2006200339A AU2006200339B2 (en) | 1995-12-01 | 2006-01-25 | Process for preparing 2-chlorothiazole compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002300672A Division AU2002300672B2 (en) | 1995-12-01 | 2002-08-21 | Process for preparing 2-chlorothiazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006200339A1 AU2006200339A1 (en) | 2006-02-16 |
| AU2006200339B2 true AU2006200339B2 (en) | 2008-03-06 |
Family
ID=36047048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006200339A Ceased AU2006200339B2 (en) | 1995-12-01 | 2006-01-25 | Process for preparing 2-chlorothiazole compounds |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2006200339B2 (en) |
-
2006
- 2006-01-25 AU AU2006200339A patent/AU2006200339B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006200339A1 (en) | 2006-02-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE456581B (en) | INTERMEDIATES FOR THE PREPARATION OF 3,4-DISUBSTITUTED 1,2,5-THIADIAZOL-1-OXIDES AND -1,1-DIOXIDES WHICH ARE H 71 RECEPTOR ANTAGONISTS | |
| EP0873326B1 (en) | Process for preparing 2-chlorothiazole compounds | |
| US20110306772A1 (en) | Process for the preparation of 2-chloro-5-chloromethyl-thiazole | |
| AU727669B2 (en) | Process for the preparation of thiazole derivatives | |
| EP0850231A1 (en) | Process for preparing a 2-chloro-5-chloromethyl-thiazole compound | |
| AU2006200339B2 (en) | Process for preparing 2-chlorothiazole compounds | |
| WO1997023469A9 (en) | Process for the preparation of 2-chloro-5-chloromethyl-thiazole | |
| EP0958286A1 (en) | Process for the preparation of thiazole derivatives | |
| CA1321594C (en) | Process for the preparation of nitroethene derivatives | |
| Barton et al. | Photochemical transformations. Part 36. Synthesis and photolytic ring contraction of mesoionic 2-alkylthiothiazol-4-ones; a new route to β-lactams | |
| AU2002300672B2 (en) | Process for preparing 2-chlorothiazole compounds | |
| SE434746B (en) | 2-PHENYL-M-DITIANDER DERIVATIVES FOR USING INTERMEDIATES WHICH SYNTHESIS OF M-DITIANDER DERIVATIVES WITH CORONARDILATING PROPERTIES | |
| Tornus et al. | Novel reactions of N-sulfonylamines with 3-dimethylamino-2 H-azirines. Competitive formation of 1, 2, 5-thiadiazoles, 1, 2, 3-oxathiazoles and acrylamidines. X-Ray molecular structure of N-(4-dimethylamino-5-methyl-2-oxo-5-phenyl-5 H-1, 2λ 6, 3-oxathiazol-2-ylidene) benzamide | |
| KR100521067B1 (en) | Preparation of thiazoles | |
| Bélai et al. | Tetrahydro‐2‐thioxo‐2H‐1, 3, 5‐thiadiazin‐4‐ones and their derivatives representing a novel heterocyclic ring system | |
| JP2627984B2 (en) | Urea derivatives | |
| KR100525941B1 (en) | Preparation of thiazoles | |
| KR970065529A (en) | A novel process for the preparation of cephalosporin intermediates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |