GB1394374A - Pyrrolo-quinoline and pyrido-quinoline derivatives - Google Patents
Pyrrolo-quinoline and pyrido-quinoline derivativesInfo
- Publication number
- GB1394374A GB1394374A GB3137674A GB3137674A GB1394374A GB 1394374 A GB1394374 A GB 1394374A GB 3137674 A GB3137674 A GB 3137674A GB 3137674 A GB3137674 A GB 3137674A GB 1394374 A GB1394374 A GB 1394374A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- quinoline
- halogen
- reacting
- 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.)
- Expired
Links
- OZKOMUDCMCEDTM-UHFFFAOYSA-N 1,7-phenanthroline Chemical class C1=CC=C2C3=NC=CC=C3C=CC2=N1 OZKOMUDCMCEDTM-UHFFFAOYSA-N 0.000 title 1
- ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 7h-pyrrolo[2,3-h]quinoline Chemical compound C1=CN=C2C(C=CN3)=C3C=CC2=C1 ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- -1 keto ester Chemical class 0.000 abstract 4
- 125000004043 oxo group Chemical group O=* 0.000 abstract 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 3
- 150000002475 indoles Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 239000012024 dehydrating agents Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000464 thioxo group Chemical group S=* 0.000 abstract 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 241001061127 Thione Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000007080 aromatic substitution reaction Methods 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 231100001184 nonphytotoxic Toxicity 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
1394374 Pyrrolo[3,2,1-i, j]-quinolines; benzo- [i, j]-quinolizines PFIZER Ltd 15 May 1973 [17 May 1972] 31376/74 Divided out of 1394373 Heading C2C Novel compounds have the Formulµ I and II wherein R is a C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl, benzoyl, hydroxy, C 1-4 alkanoyloxy or cyano group or represents one or two halogen atoms; R<SP>1</SP> and R<SP>2</SP> each independently represents hydrogen or one or more halogen, C 1-4 alkyl, phenyl, oxo or thioxo (thione) substituents; and the dotted lines represent an optional bond in each ring, with the proviso that R is other than a single chlorine atom in the 9-position in Formula II. Also claimed per se are (i) the non-phytotoxic acid addition salts of compounds of formulµ I and II and (ii) the compounds, lilolidine-2-thione, lilolidine-4-thione and julolidine-3-thione. The present pyrrolo-[3,2,1-i, j]-quinolines and pyrido-[3,2,1-i, j]-quinolines (i.e. benzo[i, j]- quinolizines) are prepared by (a) reacting an appropriately substituted indole or quinoline with a chloro-substituted acid chloride in the presence of a base to form a compound of formula which is then cyclized in the presence of AlCl 3 ; (2) reacting an appropriately substituted quinoline with acrylonitrile or a #-halopropionitrile to form a compound of formula which is hydrolysed and then cyclized in the presence of a dehydrating agent (e.g. P 2 O 5 ); (3) reacting an aniline derivative with 2 moles of acrylonitrile or a #-halopropionitrile to from a compound of formula which is then hydrolysed and cyclized as in (2); (4) reacting an appropriately substituted indole or quinoline with a keto ester, (R<SP>5</SP> = C 1-4 alkyl or phenyl, R<SP>6</SP> = H or C 1-4 alkyl) to form a compound of formula which is then cyclized in the presence of a dehydrating agent (e.g. CH 2 SO 4 or polyphosphoric acid); (5) reacting an appropriately substituted indole or quinoline with a malonic acid ester, CR<SP>7</SP>R<SP>8</SP>(CO 2 C 2 H 5 ) 2 (R<SP>7</SP> and R<SP>8</SP> are each H, C 1-4 alkyl or phenyl) to form a compound of formula and (6) conversion of existing substituents in compounds of Formulµ I and II to desired substituents, e.g. oxo to hydrogen by LiAlH 4 , oxo to thioxo by P 2 S 5 , saturation of unsaturated groups and/or replacement of halogen atoms by hydrogen atoms using catalytic hydrogenation, R = H to R = halogen, alkyl, alkanoyl or benzoyl by nuclear aromatic substitutions, halogen to cyano by cuprous cyanide, a gemdihalo group to an oxo group by hydrolysis, hydroxyl to alkanoyloxy by esterification and hydroxyl to halogen by phosphorus halides or thionyl halides. The examples describe the preparation of many specific compounds of the invention which are used in plant protection.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3137674A GB1394374A (en) | 1972-05-17 | 1972-05-17 | Pyrrolo-quinoline and pyrido-quinoline derivatives |
| MY7700082A MY7700082A (en) | 1972-05-17 | 1977-12-31 | Pyrrolo-quinoline and pyrido-quinoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3137674A GB1394374A (en) | 1972-05-17 | 1972-05-17 | Pyrrolo-quinoline and pyrido-quinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1394374A true GB1394374A (en) | 1975-05-14 |
Family
ID=10322179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3137674A Expired GB1394374A (en) | 1972-05-17 | 1972-05-17 | Pyrrolo-quinoline and pyrido-quinoline derivatives |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1394374A (en) |
| MY (1) | MY7700082A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2414046A2 (en) * | 1977-12-22 | 1979-08-03 | Du Pont | Antihypertensive pyrrolo (3,2,1-i,j)-quinoline-4-one derivs. - are 8-hydroxy-fluoroalkyl-1,2-di:hydro-4H cpds. which act by peripheral vasodilation |
| US4218448A (en) * | 1976-06-24 | 1980-08-19 | E. I. Du Pont De Nemours And Company | Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils |
| US4251659A (en) | 1977-12-22 | 1981-02-17 | E. I. Du Pont De Nemours And Company | Polyfluorohydroxyisopropyl-heterocyclic compounds |
| EP0139584A3 (en) * | 1983-10-17 | 1986-02-19 | Synthelabo | Imidazoline derivatives, their preparation and therapeutical use |
| US4833255A (en) * | 1984-05-16 | 1989-05-23 | Ciba-Geigy Corporation | Process for the preparation of indoline |
| US4886887A (en) * | 1985-11-08 | 1989-12-12 | Ciba-Geigy Corporation | Process for the preparation of indolines |
| CN102285983A (en) * | 2010-06-21 | 2011-12-21 | 中国水产科学研究院东海水产研究所 | Method for modifying flumequine into 7-hydroxyflumequine |
-
1972
- 1972-05-17 GB GB3137674A patent/GB1394374A/en not_active Expired
-
1977
- 1977-12-31 MY MY7700082A patent/MY7700082A/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4218448A (en) * | 1976-06-24 | 1980-08-19 | E. I. Du Pont De Nemours And Company | Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils |
| FR2414046A2 (en) * | 1977-12-22 | 1979-08-03 | Du Pont | Antihypertensive pyrrolo (3,2,1-i,j)-quinoline-4-one derivs. - are 8-hydroxy-fluoroalkyl-1,2-di:hydro-4H cpds. which act by peripheral vasodilation |
| US4251659A (en) | 1977-12-22 | 1981-02-17 | E. I. Du Pont De Nemours And Company | Polyfluorohydroxyisopropyl-heterocyclic compounds |
| EP0139584A3 (en) * | 1983-10-17 | 1986-02-19 | Synthelabo | Imidazoline derivatives, their preparation and therapeutical use |
| US4833255A (en) * | 1984-05-16 | 1989-05-23 | Ciba-Geigy Corporation | Process for the preparation of indoline |
| US4886887A (en) * | 1985-11-08 | 1989-12-12 | Ciba-Geigy Corporation | Process for the preparation of indolines |
| CN102285983A (en) * | 2010-06-21 | 2011-12-21 | 中国水产科学研究院东海水产研究所 | Method for modifying flumequine into 7-hydroxyflumequine |
| CN102285983B (en) * | 2010-06-21 | 2013-05-08 | 中国水产科学研究院东海水产研究所 | Method for modifying flumequine into 7-hydroxyflumequine |
Also Published As
| Publication number | Publication date |
|---|---|
| MY7700082A (en) | 1977-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1489280A (en) | Indazole derivatives | |
| GB1301224A (en) | ||
| GB1382782A (en) | Alkylarylketones processes for their preparation and compositions incorporating them | |
| GB1394374A (en) | Pyrrolo-quinoline and pyrido-quinoline derivatives | |
| US3455943A (en) | Certain 5,8-dihydro-beta-carbolines | |
| ES8206509A1 (en) | Reactive derivatives of 3-oxa-bicyclo(4.3.0)-non-1-ene-9-one, process for their preparation and their use. | |
| ES406081A1 (en) | 4-(M-benzoylphenyl)butyric acid derivatives | |
| SE7613990L (en) | ORATIC ACID DERIVATIVES TO PREPARE NEW 7-AMINO-T IAZOLYL-ACETAMIDO-CEPHALOSP | |
| ES293991A1 (en) | Intermediates for and synthesis of vitamin b and related compounds | |
| GB1495305A (en) | 3-phenyl-4-oxo-4h-benzopyran derivatives | |
| ES262677A1 (en) | Method for making benzo(a)quinolizine derivatives | |
| GB1508734A (en) | 1,3-dithiolan-2-ylidene malonate derivatives and process for the preparation thereof and usage thereof | |
| GB1186495A (en) | 0-[3-(4-Fluorobenzoyl) Proplyl]-4-Substituted Piperazines, their Acid Addition Salts and their method of preparation | |
| SE7415015L (en) | METHODS OF PRODUCING NEW 2-PHENYLHYDRAZINO-THIAZOLINES OR -TIAZINES | |
| GB1365770A (en) | Basically substituted 1/2h/-phtalazinone derivatives and proce sses for the production thereof | |
| GB1390304A (en) | 1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonine | |
| GB1441941A (en) | Process for the preparation of 5-substituted resorcinols and related intermediates | |
| GB1357212A (en) | Benzothiophene derivatives and process for preparing the same | |
| HUT43612A (en) | Process for production of new derivatives of peneme and medical preparatives containing thereof | |
| GB993156A (en) | Quinolizine derivatives | |
| GB2012762A (en) | 5,6-dihydro prostacyclin derivatives | |
| ES485801A1 (en) | Process for preparing cyclo-1,3,2-oxazaphosphoryl derivatives | |
| GB1301366A (en) | ||
| GB1456267A (en) | Benzofuran derivatives and their use as optical brighteners | |
| US4238605A (en) | 2-Decarboxy-2-aminomethyl-9-deoxy-5,9α-epoxy-4,5-cis-17,18-tetradehydro-PGF1 compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930514 |