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WO2010122793A1 - Procédé de production d'un dérivé de pyrazine et intermédiaire pour la production - Google Patents

Procédé de production d'un dérivé de pyrazine et intermédiaire pour la production Download PDF

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Publication number
WO2010122793A1
WO2010122793A1 PCT/JP2010/002897 JP2010002897W WO2010122793A1 WO 2010122793 A1 WO2010122793 A1 WO 2010122793A1 JP 2010002897 W JP2010002897 W JP 2010002897W WO 2010122793 A1 WO2010122793 A1 WO 2010122793A1
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alkyl group
general formula
producing
derivative according
derivative
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Japanese (ja)
Inventor
雅次 織田
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/16—Halogen atoms; Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/18—Oxygen or sulfur atoms

Definitions

  • the present invention relates to a method for producing a 3-haloalkyl-2-halogenopyrazine derivative useful as an intermediate for pharmaceuticals, agricultural chemicals, etc., particularly as an intermediate for producing agricultural and horticultural acaricides and fungicides, its synthetic intermediate, and
  • the present invention relates to a method for producing a synthetic intermediate.
  • 3-Haloalkyl-2-halogenopyrazine derivatives are used as intermediates for pharmaceuticals, agricultural chemicals, etc., especially for agricultural and horticultural acaricides (for example, see Patent Document 1) and agricultural and horticultural fungicides (for example, Patent Document 2).
  • Useful as an intermediate of As a production method thereof there is a production method in which 2-chloro-3-iodopyrazine is substituted with 2-chloro-2,2-difluoroacetic acid methyl ester, potassium fluoride and copper iodide, and the iodine atom is substituted with a trifluoromethyl group. It is known (for example, see Non-Patent Document 1).
  • Non-Patent Document 1 In the method of Non-Patent Document 1, it is necessary to introduce an iodine atom at an appropriate position of the pyrazine ring in advance, use of expensive 2-chloro-2,2-difluoroacetic acid methyl ester, The above copper iodide is necessary, its removal is difficult, and the reaction temperature is high, so that it is not necessarily an industrially advantageous production method.
  • the reports of Non-Patent Documents 2 and 3 have no disclosure or suggestion about the derivative according to the present invention and the production method thereof.
  • An object of the present invention is to provide a novel and industrially advantageous production method for 3-haloalkyl-2-halogenopyrazine derivatives useful as intermediates for pharmaceuticals and agricultural chemicals.
  • a novel dihydropyrazinone derivative is obtained by reacting an epoxy derivative having a specific structure with 1,2-ethylenediamine or an acid salt thereof, and then dehydrogenating or dehydrogenating it. It has been found that an industrially useful 3-haloalkyl-2-halogenopyrazine derivative can be efficiently produced by oxidizing to a novel hydroxypyrazine derivative and further halogenating the hydroxyl group of this derivative. Furthermore, the present inventors have found that the intermediate dihydropyrazinone derivative and hydroxypyrazine derivative are novel compounds not described in the literature, and have completed the present invention.
  • R 1 is as defined above, Y represents a halogen atom
  • the objective compound can be produced efficiently and economically on an industrial scale by using an easily available reagent and without using conventionally used copper iodide.
  • R 1 is halo (C 1 -C 6) alkyl group, preferably fluoro (C 1 -C 6) alkyl group, more preferably perfluoro (C 1 -C 6 )
  • An alkyl group particularly preferably a perfluoro (C 1 -C 3 ) alkyl group, and most preferably a trifluoromethyl group.
  • X is a halogen atom, preferably a chlorine atom or a fluorine atom, and most preferably a fluorine atom.
  • Y is a halogen atom, preferably a bromine atom or a chlorine atom, and most preferably a chlorine atom.
  • halogen atom In the definition of the substituents of the compounds represented by the general formulas (I) to (IV) of the present invention, “halogen atom”, “halogeno” and “halo” are fluorine atom, chlorine atom, bromine atom or iodine atom.
  • a “halo (C 1 -C 6 ) alkyl group” which may be the same or different, and represents a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms.
  • trifluoromethyl group for example, trifluoromethyl group, difluoromethyl group, perfluoroethyl group, perfluoroisopropyl group, perfluoronormal butyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2,2,2-trifluoroethyl Group or a 2,3-dibromopropyl group.
  • “Fluoro (C 1 -C 6 ) alkyl group” means a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more fluorine atoms, and includes, for example, a trifluoromethyl group, Examples thereof include a difluoromethyl group, a perfluoroethyl group, a perfluoroisopropyl group, or a 2,2,2-trifluoroethyl group.
  • the term “perfluoro (C 1 -C 3 ) alkyl group” refers to a linear or branched alkyl group having 1 to 3 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms. Examples thereof include a methyl group, a perfluoroethyl group, and a perfluoroisopropyl group.
  • 1,2-ethylenediamine or an acid salt thereof can be used in an amount of 0.1 to 100 times mol, preferably 0.5 to 10 times mol, of the epoxy derivative represented by the general formula (II). More preferably, it is in the range of 0.9 to 5 moles.
  • the inert solvent used is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane
  • aromatic hydrocarbons such as benzene, toluene, and xylene.
  • Halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; linear or cyclic ethers such as diethyl ether, t-butyl methyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; methanol, ethanol, n- Alcohols such as propanol and 2-propanol; Amides such as dimethylformamide and dimethylacetamide; Nitriles such as acetonitrile; Esters such as ethyl acetate, butyl acetate, pentyl acetate and ethyl propionate; 1,3-dimethyl 2-inert solvent such as imidazolidinone or water can be exemplified, and these solvents may be used alone or as a mixture of two or more inert solvents.
  • linear or cyclic ethers such as diethyl ether, t-butyl methyl ether, dioxan
  • a base or an acid salt thereof may be added.
  • the base include monoethylamine, diethylamine, triethylamine, tributylamine, pyrrolidine, piperidine, morpholine, pyridine, 4-dimethylaminopyridine, and lutidine.
  • organic bases such as pyrrole; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkali metal alkoxides such as sodium methoxide and sodium ethoxide.
  • base acid salts include acid salts of organic bases such as diethylamine hydrochloride, pyrrolidine hydrochloride and pyridine sulfate; ammonium salts such as ammonium acetate; carbonates such as sodium bicarbonate and potassium carbonate; sodium fluoride
  • alkali metal halides such as: phosphates such as potassium monohydrogen phosphate and trisodium phosphate. Of these, organic bases and alkali metal hydroxides are preferred.
  • bases or acid salts thereof can be appropriately selected within a range of 0.01 to 100 times the epoxy derivative represented by the general formula (II), but preferably within a range of 1 to 20 times. .
  • phase transfer catalyst such as a quaternary ammonium salt such as tetrabutylammonium bromide or a crown ether such as 18-crown-6 can be used, which is represented by the general formula (II). It can be appropriately selected within a range of 0.001 to 0.1 moles relative to the epoxy derivative.
  • the reaction temperature may be appropriately selected within the range of ⁇ 76 ° C. to the reflux temperature of the inert solvent used, but is preferably selected within the range of ⁇ 76 ° C. to 80 ° C.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 100 hours.
  • the reaction proceeds even in the presence of oxygen in the air, but the reaction may be performed in an inert gas atmosphere such as nitrogen gas or argon gas.
  • an inert gas atmosphere such as nitrogen gas or argon gas.
  • a by-product in the state of hemiaminal shown in the above may be partially produced, but it may be used in the next step as it is.
  • the epoxy derivative used for this reaction is a low boiling point compound, it can also carry out using an autoclave.
  • the dihydropyrazinone derivative represented by the general formula (I) may be isolated from the reaction system containing the target product by a conventional method, and this is purified by recrystallization, column chromatography or the like as necessary. By doing so, the target product can be manufactured.
  • the dihydropyrazinone derivative represented by the general formula (I) can be used for the next reaction without isolation.
  • the epoxy derivative represented by the general formula (II) can be produced by a known method, for example, the method described in GB904877 (1960) or in accordance therewith.
  • the inert solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane
  • aromatic hydrocarbons such as benzene, xylene and toluene
  • diethyl Linear or cyclic ethers such as ether, t-butyl methyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane
  • amides such as dimethylformamide and dimethylacetamide
  • nitriles such as acetonitrile and propionitrile
  • acetone and methyl Linear or cyclic ketones such as isobutyl ketone and cyclohexanone
  • esters such as ethyl acetate and butyl acetate
  • alcohols such as methanol, ethanol, n-propanol and i-propanol
  • a base or an acid salt thereof may be added to accelerate the reaction.
  • the base include monoethylamine, diethylamine, triethylamine, tributylamine, pyrrolidine, piperidine, morpholine, pyridine, picoline, 4-dimethylaminopyridine, and lutidine.
  • organic bases such as pyrrole; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkali metal alkoxides such as sodium methoxide and sodium ethoxide.
  • base acid salts include acid salts of organic bases such as diethylamine hydrochloride, pyrrolidine hydrochloride and pyridine sulfate; ammonium salts such as ammonium acetate; carbonates such as sodium bicarbonate and potassium carbonate; phosphorus Examples thereof include phosphates such as potassium monohydrogen acid and trisodium phosphate.
  • organic bases such as diethylamine hydrochloride, pyrrolidine hydrochloride and pyridine sulfate
  • ammonium salts such as ammonium acetate
  • carbonates such as sodium bicarbonate and potassium carbonate
  • phosphorus examples thereof include phosphates such as potassium monohydrogen acid and trisodium phosphate.
  • organic bases and most preferred are pyridines optionally substituted with an alkyl group such as picoline.
  • bases or acid salts thereof can be appropriately selected in the range of 0.01 to the amount of solvent with respect to the dihydropyrazinone derivative represented by the general formula (I), preferably in the range of 1 to 20 times. It is.
  • the reaction temperature may be appropriately selected within the range of ⁇ 30 ° C. to the reflux temperature of the inert solvent used, but is preferably selected within the range of 0 to 80 ° C.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 200 hours.
  • additives include manganese compounds such as manganese dioxide; chromic acids such as sodium chromate; lead compounds such as lead tetraacetate; mercury compounds such as mercury oxide; oxidizing agents such as osmium tetroxide, ruthenium tetroxide, and selenium dioxide.
  • Metal halides such as iron chloride, copper iodide, copper chloride, magnesium chloride, zinc chloride and boron fluoride; halogens such as iodine and bromine; transitions such as palladium, platinum, iridium, rhodium, ruthenium, selenium and rhenium Metal compounds; quinone-based oxidizing agents such as DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone); peroxides such as hydrogen peroxide, perbenzoic acid, m-chloroperbenzoic acid; Carbonates such as potassium, sodium carbonate, sodium bicarbonate, calcium carbonate, barium carbonate, ammonium carbonate; Metal oxides such as cupric oxide, iron oxide and palladium oxide; haloimides such as N-chlorosuccinimide, N-bromosuccinimide and diiodohydantoin; sulfur atoms, oxygen, activated carbon, silic
  • the metal compound such as palladium and platinum
  • the metal itself can be used.
  • activated carbon, silica gel, alumina, diatomaceous earth, pumice, barium sulfate, or polyaniline JOC, 1997, 62, 1072-1078, T L., 48 (2007) 2729-2732
  • Pd / C and Pt / C supported on activated carbon are preferred.
  • the metal may be zero-valent or may be appropriately oxidized like Pd (OH) 2 or PtO 2 , but preferably zero-valent.
  • Preferred additives include metal halides, carbonates, halogens, transition metal compounds, and activated carbon. These additives can be used alone or in admixture of two or more.
  • additives can be appropriately selected in the range of 0.001 to 10 times mol, preferably 0.01 to 2 times mol of the dihydropyrazinone derivative represented by the general formula (I). A range is preferred.
  • this reaction may be performed in an oxidizing atmosphere such as oxygen or air bubbling.
  • the hydroxypyrazine derivative represented by the general formula (III) may be isolated from the reaction system containing the target product by a conventional method, and this is purified by recrystallization, column chromatography or the like as necessary. Thus, the target product can be produced. Further, the hydroxypyrazine derivative represented by the general formula (III) can be used in the next reaction without isolation.
  • the reaction does not need to use a solvent, but can be carried out in the presence of a catalyst or in an inert solvent, if necessary.
  • the catalyst examples include basic solvents such as dimethylformamide and dimethylacetamide, and organic bases such as N, N-dimethylaniline and N, N-diethylaniline. It is appropriately selected within the range of 0.01 to 1 molar equivalent.
  • the inert solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane
  • aromatic hydrocarbons such as benzene, xylene and toluene
  • diethyl Chain or cyclic ethers such as ether, t-butyl methyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane
  • Amides such as dimethylformamide and dimethylacetamide; Nitriles such as acetonitrile and propionitrile; Acetone Linear or cyclic ketones such as methyl isobutyl ketone and cyclohexanone; esters such as ethyl acetate and butyl acetate; amide solvents such as dimethylformamide and dimethylacetamide; 1,3-dimethyl-2-imidazolidinone, and It can be
  • halogenating agent examples include thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, phenylphosphonic dichloride, phosgene, and phosphorus tribromide. These halogenating agents can be appropriately selected in the range of 1 to 20 times molar equivalent to the hydroxypyrazine derivative represented by the general formula (III), but preferably in the range of 1 to 3 times the molar. .
  • the reaction temperature may be appropriately selected within the range of the reflux temperature of the inert solvent or halogenating agent used from 0 ° C., but is preferably selected from the range of 50 to 180 ° C.
  • reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 100 hours.
  • the reaction proceeds even in the presence of oxygen in the air, but may be performed in an inert gas atmosphere such as nitrogen gas or argon gas.
  • the halogenopyrazine derivative represented by the general formula (IV) may be isolated from the reaction system containing the target product by a conventional method, and this is purified by recrystallization, column chromatography or the like as necessary.
  • the target product can be produced.
  • the compound of the present invention produced in each step can be obtained from the reaction solution by a conventional method. However, when it is necessary to purify the compound, any of distillation, suspension washing, recrystallization, column chromatography, etc. It can be separated and purified by the purification method. Moreover, it can also be separated into a salt and purified using an inorganic acid such as hydrochloric acid.
  • the 3-haloalkyl-2-halogenopyrazine derivative obtained by the production method of the present invention can be easily derived into a 3-haloalkylpyrazin-2-ylcarboxylic acid ester derivative by, for example, the method shown in Reference Example and further amidated.
  • useful compounds such as agricultural and horticultural acaricides (Patent Document 1) and agricultural and horticultural fungicides (Patent Document 2) can be produced.
  • Example 1 Production of 3-trifluoromethyl-5,6-dihydropyrazin-2 (1H) -one-1 Hexafluoropropylene oxide (1.7 g, 10.2 mmol) was blown into a solution of 1,2-ethylenediamine (1.8 g, 30 mmol) monohydrate in t-butyl methyl ether (25 ml) at ⁇ 10 ° C. to 0 ° C. The mixture was stirred for 30 minutes at room temperature for 1 hour.
  • Example 3 Preparation of 3-trifluoromethyl-5,6-dihydropyrazin-2 (1H) -one-3 Hexafluoropropylene oxide (2 g, 12 mmol) was blown into a mixed solution of ethylenediamine (1.8 g, 30 mmol) in chloroform (24 ml) and water (1 ml, 56 mmol) at 0 to 15 ° C. under ice cooling. After further stirring at 0 ° C. for 30 minutes and at room temperature for 2 hours, water was added to separate the layers. After sodium fluoride was added to the organic layer and stirred, the filtered filtrate was concentrated under reduced pressure. The residue was recrystallized from n-hexane / chloroform to obtain the title compound as a pale yellow solid. Yield; 1.7g Yield; 85%
  • Example 8 Production of 2-hydroxy-3-trifluoromethylpyrazine-4 Hexafluoropropylene oxide (5 g, 30 mmol) was blown into a mixed solution of ethylenediamine (5 g, 83 mmol) in ethyl acetate (30 ml) and water (2 ml) at 0 to 15 ° C. under ice cooling. The mixture was further stirred at 0 ° C. for 30 minutes and at room temperature for 2 hours, water (10 ml) was added and the mixture was stirred for 1 hour, and the liquid separation and organic layer were washed with saturated brine.
  • ethylenediamine 5 g, 83 mmol
  • the filtrate was transferred to a separatory funnel to remove the aqueous layer, washed with water, and then washed with saturated saline.
  • the obtained organic layer was dried over anhydrous sodium sulfate, and suction filtered through a Buchner funnel with celite and silica gel. The residue was washed with 900 ml t-butyl methyl ether.
  • the obtained filtrate and washing solution were combined and concentrated on a warm water bath at 40 ° C. at 150 mmHg to obtain 68 g of a brown oily substance.
  • the inside of the reaction vessel was replaced twice with argon gas and twice with carbon monoxide gas, and then charged with carbon monoxide gas at an initial pressure of 20 kg / cm 2 and reacted at 120 ° C. for 2 hours.
  • the temperature was returned to room temperature, the catalyst was removed, and the filtrate was concentrated.
  • the residue was extracted with t-butyl-methyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • the inorganic material was filtered and concentrated. The residue was distilled under reduced pressure to obtain methyl 3-trifluoromethylpyrazine-2-carboxylate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention a pour objet un nouveau procédé de production d'un dérivé de 3-halogénoalkyl-2-halogénopyrazine utile en tant qu'intermédiaire pour la production d'agents pharmaceutiques, de produits agrochimiques et autres. L'invention a pour objet spécifique un procédé de production d'un dérivé de 3-halogénoalkyl-2-halogénopyrazine représenté par la formule générale (IV), qui est caractérisé par : la réaction d'un dérivé époxy représenté par la formule générale (II) avec de la 1,2-ethylènediamine ou l'un de ses sels d'acide pour produire un dérivé de dihydropyrazinone représenté par la formule générale (I); la conversion du dérivé de dihydropyrazinone (I) en un dérivé d'hydroxypyrazine représenté par la formule générale (III) par déshydrogénation ou oxydation; et l'halogénation du dérivé d'hydroxypyrazine (III).
PCT/JP2010/002897 2009-04-23 2010-04-22 Procédé de production d'un dérivé de pyrazine et intermédiaire pour la production Ceased WO2010122793A1 (fr)

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JP2009104858 2009-04-23

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016104755A1 (fr) * 2014-12-25 2016-06-30 旭硝子株式会社 Procédé de production d'un dérivé de dihydropyrazinone
WO2024171716A1 (fr) * 2023-02-17 2024-08-22 株式会社トクヤマ Procédé de production de 2-chloro-5,6-diphénylpyrazine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007072999A1 (fr) * 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Derives pyrazinecarboxamide et agents de lutte contre les parasites les contenant
JP2009242244A (ja) * 2008-03-28 2009-10-22 Nippon Nohyaku Co Ltd ピラジン誘導体類の製造方法及びその中間体類

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007072999A1 (fr) * 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Derives pyrazinecarboxamide et agents de lutte contre les parasites les contenant
JP2009242244A (ja) * 2008-03-28 2009-10-22 Nippon Nohyaku Co Ltd ピラジン誘導体類の製造方法及びその中間体類

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ISHIKAWA, N. ET AL.: "Preparation of perfluoroalkylated benzoheterocyclic compounds using hexafluoro-1,2-epoxypropane", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 50, no. 8, 1977, pages 2164 - 2167 *
MASUDA, H. ET AL.: "Synthesis of alkoxy-, (alkylthio)-, phenoxy-, and (phenylthio) pyrazines and their olfactive properties", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 34, no. 2, 1986, pages 377 - 381 *
PATEL, M. ET AL.: "Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 10, no. 15, 2000, pages 1729 - 1731 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016104755A1 (fr) * 2014-12-25 2016-06-30 旭硝子株式会社 Procédé de production d'un dérivé de dihydropyrazinone
CN107108528A (zh) * 2014-12-25 2017-08-29 旭硝子株式会社 二氢吡嗪酮衍生物的制造方法
WO2024171716A1 (fr) * 2023-02-17 2024-08-22 株式会社トクヤマ Procédé de production de 2-chloro-5,6-diphénylpyrazine

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