В 40 Взаимодействие этилового эфира 2-метил-5,6,7,8-тетрафторхромон-3-карбоновой кислоты и 3-ацетимидоил-4-гидрокси-5,6,7,8-тетрафторкумарина с S-нуклеофилами [] = Reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate and 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with S-nucleophiles / И. Т. Базыль, С. П. Кисиль, С. Н. Фролов, Я. В. Бургарт, В. И. Салоутин // Изв. АН. Сер. Химическая. - 1999. - N 8. - С. 1557-1561 . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Щ 61 Щербаков, К. В. Реакции 5,6,7,8-тетрафтор-2(3)-этоксикарбонилхромонов с метиламином [] = Reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with benzylamine and aniline / К. В. Щербаков, Я. В. Бургарт, В. И. Салоутин // Изв. АН. Сер. Химическая. - 2005. - N 9. - 2093-2098: рис. - Библиогр. : с. 2098 (13 назв.) . - ISSN 0002-3353 Рубрики: Химические науки Аннотация: 5.6.7.8-Тетрафтор-2-этоксикарбонилхромон реагирует с метиламином неоднозначно в зависимости от использованного растворителя и количества амина: в ДМСО и MeCN - первоначальнопо положению С(7) с замещением атома фтора, и далее по центрам С(2) и/или С(9), а в этаноле - по центру С(2) с раскрытием пиронового цикла. 2-Метил-5,6,7,8-тетрафтор-3-этоксикарбонилхромон реагирует с метиламином независимо от растворителя с раскрытием хромонового цикла и промежуточным образованием этил-2-(1-метиламино)этилиден-3-(2-гидрокси-3,4,5,6-тетрафторфенил)-3-оксопропионата, из которого в результате внутримолекулярной циклизации получен 3-(1-метил-амино)этилиден-5,6,7,8-тетрафтор-3.4-дигидро-2H-бензопиран-2,4-дион |
N 52 New reactions of fluorinated 2,4-dioxoesters with aromatic aldehydes [Electronic resource] / M. V. Pryadeina, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2006. - Vol. 16, № 3. - P188-189 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 4-Polyfluoroalkyl 2,4-dioxobutanoates react with aromatic aldehydes to give 4-aryl-2,6-dihydroxy-2,6-di (fluoroalkyl)-3,5-diethoxalyltetrahydropyrans 3a,b, whereas the reaction of 4-pentafluorobenzoyl 2,4-dioxobutanoate with benzaldehyde gives 5,6,7,8-tetrafluoro-1-phenyl-1H-furo[3,4-b]chromene-3,9-dione 4. \\\\Expert2\\nbo\\Mendeleev Communications\\2006, v.16, p.188.pdf |
U 52 Unexpected formation of pyridazine-5,6-dione derivatives in the reactions of 3-arylhydrazono-2,4-dioxo-4-pentafluorophenylbutanoates with hydrazines [Electronic resource] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2005. - Vol. 15, № 6. - P252-253 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDAZINES Аннотация: The reactions of 3-arylhydrazono-2,4-dioxo-4-pentafluorophenylbutanoates with hydrazine hydrate and phenylhydrazine resulted in the formation of 4-arylazo-3-pentafluorophenyl-1,2-dihydro-5H,6H-pyridazine-5,6-diones or 6-aryl-2-phenyl-7,8,9,10-tetrafluoro-2,3,4,6-tetrahydropyridazino[4,3-c]cinnoline-3,4-dione. \\\\Expert2\\nbo\\Mendeleev Communications\\2005, v.15, p.252.pdf |
S 98 Synthesis of fluorine-containing 2-(1-aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic acids [Electronic resource] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 9. - P1374-1376. - Библиогр. : с. 1376 (9 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Acid hydrolysis of ethyl 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetates gives 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2,2-dihydroxyacetic acids which undergo dehydration on heating in toluene to afford 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic acids. Reactions of the latter with excess morpholine result in replacement of two fluorine atoms in positions 5 and 7 by the amine residues. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (9), 1374-1376.pdf |
П 99 5,6,7,8-Tetrafluoro-4-hydroxycoumarin derivatives in reactions with o-phenylenediamine [Electronic resource] / Ya. V. Burgart, K. V. Shcherbakov, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1237-1239. - Библиогр. : с. 1239 (5 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TETRAFLUORO -- HYDROXYCOUMARINES Аннотация: The reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with o-phenylenediamine occur with pyrone heterocycle cleavage and formation of substituted benzodiazepin-2-ones. 5,6,7,8-Tetrafluoro-4-hydroxycoumarin affords 4-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-2-one, 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin produces 3-(3,4,5,6-tetrafluoro-2-hydroxybenzoyl)-4-methyl-1,2-dihydro-1H-1,5-benzodiazepin-2-one, and 3-acetyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin yields both these heterocycles. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1237-1239.pdf |
N 52 New approach to [a]-fused fluoroquinolones: the synthesis of 5-oxo-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinolines [Electronic resource] / E. Tsoi, V. N. Charushin, E. V. Nosova, G. N. Lipunova, A. V. Tkachev // Mendeleev Communications. - 2001. - Vol. 11, № 2. - P53-54 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of N-(ethoxycarbonyl)methyl substituted ethyl 6,7-difluoro-, 6,7,8-trifluoro- and 5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylates with methyl methacrylate results in the [3 + 2] adducts, hexahydropyrrolo[1,2-a]quinolones, which can be precursors of [a]-fused fluoroquinolones.?????? \\\\expert2\\nbo\\Mendeleev Communications\\2001, v.11, N 2. p.53.pdf |
S 98 Synthesis of 2-(1-alkyl(aryl)-4-oxo-5,6,7,8-tetrafluoro-1,4-dihydroquinolin-3-yl)glyoxylic acid derivatives [Text] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2001. - Vol. 108, № 2. - P187-194 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Methods for synthesis of previously unknown 2-(1-alkyl(aryl)-4-oxo-5,6,7,8-tetrafluoro-1,4-dihydroquinolin-3-yl)glyoxylic acids and their esters from the copper chelate of ethyl pentafluorobenzoylpyruvate were developed. 1-Aryl(alkyl)-3-ethoxalyl-5,6,7,8-tetrafluoro-quinolin-4-ones react with o-phenylenediamine and o-aminophenol to give the corresponding quinolin-3-ylquinoxalones and quinolin-3-ylbenzoxazines. The same heterocycles act with o-aminothiophenol to yield ethyl-2-(7-(2-aminophenylthio)-1-aryl-5,6,8-trifluoro-quinolon-3-yl)-2-(2-mercaptophenylimino)glioxylates. Interaction of 1-aryl-3-ethoxalyl-(heteryl)-5,6,7,8-tetrafluoroquinolones with morpholine gives 7-mono- and 5,7-disubstituted products depending on the reaction conditions???? |
U 52 Unexpected synthesis of 3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one [Electronic resource] / Ya. V. Burgart, M. V. Pryadeina, O. G. Kuzueva, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2001. - Vol. 11, № 3. - P119-120 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of ethyl pentafluorobenzoylacetate with benzaldehyde in the presence of a base affords 3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one in contrast to fluoroalkyl-containing 3-oxo esters yielding 3,5-dialkoxycarbonyl-2,6-dihydroxy-2,6-difluoroalkyl-4-phenyltetrahydropyranes under the same conditions???? |
R 30 Reactions of fluorine-containing 3-oxo esters with aldehydes [Text] / M. V. Pryadeina, O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin, K. A. Lyssenko, M. Yu. Antipin // Journal of Fluorine Chemistry. - 2002. - Vol. 17, № 1. - P1-7 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkylcontaining 3-oxo esters react with aldehydes to form 2-benzylidene-3-fluoroacyl-esters or 4-aryl(alkyl)-3,5-dialkoxycarbonyl-2,6-dihydroxy-2,6-di(fluoroalkyl)tetrahydropyranes depending on the conditions. Ethyl pentafluorobenzoylacetoacetate with benzaldehyde affords 3,5-diethoxy-carbonyl-4-phenyl-2-pentafluorophenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one |
R 30 Reaction of Fluoro-containing 3-Oxoesters with Benzaldehyde [Electronic resource] / M. V. Pryadeina, O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2002. - Vol. 38, № 2. - P224-231 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated 3-oxoesters in reactions with benzaldehyde depending on conditions afford either 2-benzylidene-3-fluoroalkyl-3-oxoesters or 3,5-dialkoxycarbonyl-2,6-dihydroxy-2,6-difluoroalkyl-4-phenyltetrahydropyrans. The latter were also obtained by treating 3-oxoesters with 2-benzylidene-3-oxoesters. Pentafluorobenzoylacetate with benzaldehyde furnishes 3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2002, 38 (2), 224.pdf |
F 71 Fokin, A. S. Fluorine-containing 3-arylhydrazono-2,4-dioxobutanoates in reactions with difunctional nucleophiles [Electronic resource] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 6. - P887-896 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Arylhydrazono-4-polyfluoroalkyl-2,4-dioxobutanoates reacted with hydrazines to give ethyl 4-aryldiazeno-3-polyfluoroalkyl-1H-pyrazole-5-carboxylates, while analogous reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates resulted in the formation of 4-aryldiazeno-3-pentafluorophenyl-1,2-dihydropyridazine-5,6-diones or 6-aryl-7,8,9,10-tetrafluoro-2-phenyl-2,4a,6,10b-tetradropyridazo[4,3-c]cinnoline-3,4-diones, depending on the conditions. Cyclocondensation of ethyl 3-arylhydrazono-4-polyfluoroalkyl(or pentafluorophenyl)-2,4-dioxobutanoates with ethylenediamine led to 3-[1-arylhydrazono-2-oxo-2-polyfluoroalkyl(or pentafluorophenyl)ethyl]-5,6-dihydropyrazin-2(1H)-ones, and 3-[1-arylhydrazono-2-oxo-2-polyfluoroalkyl(pentafluorophenyl)ethyl]benzoxazin-2-ones were formed in the condensation with o-aminophenol. Pentafluorophenyl-substituted heterocycles were found to undergo intramolecular ring closure to give 3-hetaryl-substituted 1-aryl-5,6,7,8-tetrafluoro-1,4-dihydrocinnolin-4-ones. The reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates with o-aminobenzenethiol gave 3-[7-(2-aminophenylsulfanyl)-1-aryl-5,6,8-trifluoro-4-oxo-1,4-dihydrocinnolin-3-yl]benzothiazin-2-ones; 8a-hydroxy-11,12,13,14-tetrafluoro-10-(4-methoxyphenyl)-2,3,4,5,6,7,8a,10-octahydropyrazino[1?,2?:4,5][1,4]diazepino[6,7-c]cinnolin-8-one was isolated in the condensation of ethyl 3-(4-methoxyphenylhydrazono)-4-pentafluorophenyl-2,4-dioxobutanoate with N-(2-aminoethyl)ethane-1,2-diamine ?? \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (6), 887.pdf |
S 53 Shcherbakov, K. V. Transformations of 5,6,7,8-tetrafluoro-2-ethoxycarbonylchromone under the action of primary amines [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 5. - P766-772 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5,6,7,8-TETRAFLUORO -- CHROMONES Аннотация: 5,6,7,8-Tetrafluoro-2-ethoxycarbonylchromone in aprotic polar solutions formed by nucleophilic aromatic ipso-substitution 7-alkyl(aryl)amino-5,6,8-trifluorochromones. This transformation in ethanol depended on the reactivity of the acting amine: with stronger nucleophiles, aliphatic amines, an opening of the ?-pyrone ring occurred, with aromatic amines 7-monosubstituted chromones were the main products, and the open-chain esters formed in lesser amount \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (5), 766.pdf |
S 53 Shchegol'kov, E. V. Reactions of 5,6,7,8-Tetrafluoro-4-hydroxy-2H-chromen-2-ones with methylamine [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 12. - P1838-1844 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5,6,7,8-Tetrafluoro-4-hydroxy-2H-chromen-2-one reacts with methylamine to give methylammonium 5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, regardless of the solvent. The reaction of 3-acetyl-5,6,7,8-tetrafluoro-4-hydroxy-2H-chromen-2-one with the same amine in ethanol or acetonitrile leads to the formation of methylammonium 3-acetyl-5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, while in dimethyl sulfoxide 5,6,8-trifluoro-7-methylamino-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is formed. The latter is also formed in the reaction of 5,6,7,8-tetrafluoro-4-hydroxy-3-(1-iminoethyl)-2H-chromen-2-one with methylamine in DMSO, whereas in ethanol and acetonitrile 5,6,7,8-tetrafluoro-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is obtained. 5,6,7,8-Tetrafluoro-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione reacts with methylamine, yielding 7-mono-or 5,7-bis(methylamino)-substituted derivatives \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (12), 1838.pdf |
3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles [Electronic resource] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 9. - P1354-1358 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Ethoxy- and 3-arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates undergo cyclization by the action of hydrazine hydrate and phenylhydrazine to give ethyl 4-pentafluorobenzoylpyrazole-5-carboxylates. The reaction of 3-ethoxymethylidene-2,4-dioxo-4-pentafluorophenylbutanoate with o-phenylene-diamine leads to formation of 3-[2-(2-aminophenylamino)-1-pentafluorobenzoylethenyl]-1,2-dihydroquinoxa-lin-2-one. 3-Arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates react with o-phenylenediamine to afford 3-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)-1,2-dihydroquinoxalin-2-ones and/or 3-(2-arylamino-1-pentafluorobenzoylethenyl)-1,2-dihydroquinoxalin-2-ones \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (9), 1374-1376.pdf |
K 49 Kisil', S. P. New Fluoroaryl-containing beta,beta'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones [Electronic resource] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 10. - P1455-1462 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these ,'-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-triflu \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (10), 1455.pdf |
S 98 Synthesis of N-substituted 2-(5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)glyoxylic acids [Electronic resource] / G. A. Obanin, A. S. Fokin, Ya. V. Burgart, O. V. Ryzhkov, Z. E. Skryabina, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2000. - Vol. 49, № 7. - P1231-1236 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ETHYL PENTAFLUOROBENZOYLPYRUVATE -- SYNTHESIS Аннотация: Methods for the synthesis of the earlier unknownN-substituted 2-(5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)glycoxylic acids their esters from copper chelate of ethyl pentafluorobenzoylpyruvate were developed. The structure of intermediate ethyl 4-(R-amino)-2-oxo-3-pentafluorobenzoylbut-3-enoates is discussed \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2000, 49 (7), 1231.pdf |
R 30 Reactions of 1-aryl(alkyl)-3-ethoxalyl-5,6,7,8-tetrafluoro-1,4-dihydrocinnolin(quinolin)-4-ones with aromatic dinucleophiles [Electronic resource] / A. S. Fokin, Ya. V. Burgart, O. V. Ryzhkov, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 4. - P689-692 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The title compounds react with o-phenylenediamine and o-aminophenol at the ethoxalyl fragment to form heteryl-substituted quinoxalones and benzooxazinones, respectively. o-Aminobenzenethiol acts as both an S-nucleophile replacing the F atom and an N-nucleophile replacing the carbonyl group in the ethoxalyl fragment. Under more drastic conditions, cyclization proceeds to form benzothiazinones \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (4), 689.pdf |
S 53 Shcherbakov, K. V. Reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with benzylamine and aniline [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 7. - P1215-1219 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5,6,7,8-Tetrafluoro-4-hydroxycoumarin reacted with benzylamine under mild conditions to give a stable salt, while its refluxing with aniline or benzylamine in xylene afforded 5,6,7,8-tetrafluoro-4-phenyl(benzyl)aminocoumarins. Reactions of 3-acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins with benzylamine followed different pathways, depending on the solvent. Condensation at the acyl substituent can be accompanied by replacement of the F atom in position 7. 3-Acetylcoumarin formed a salt, while 3-acetimidoylcoumarin yielded a 7-monosubstituted product. 3-Acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins reacted with aniline to give only 5,6,7,8-tetrafluoro-4-hydroxy-3-(N-phenylacetimidoyl)coumarin \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (7), 1215-1219.pdf |
R 30 Reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate and 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with S-nucleophiles [Electronic resource] / I. T. Bazyl, S. P. Kisil', S. N. Frolov, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, № 8. - P1537-1541 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate with mercaptoacetic acid and 1,2-ethanedithiol afforded C(7)-substitution products. The above-mentioned chromone reacted with 2-mercaptoethanol to yield 7-mono- or 5,7,8-trisubstituted products depending on the reaction conditions. The reaction of 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with 2-mercaptoethanol afforded a 5,7,8-trisubstituted produect. The acyl-lactone rearrangement of mono- and trisubstituted chromones yielded the corresponding coumarins \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (8), 1537.pdf |