I-69 Interaction of 3-ethoxycarbonyl(carboxy)-substituted 5,6,7,8-tetrafluorochromones with N-nucleophiles synthesis of fluorocoumarins [Text] / V. I. Saloutin, Z. E. Skryabina, I. T. Bazyl, S. P. Kisil' // Journal of Fluorine Chemistry. - 1999. - Vol. 94, N 1. - P83-90 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
T 44 The selective ortho-methoxylation of pentafluorobenzoic acid - a new way to tetrafluorosalicylic acid and its derivatives [Text] / I. T. Bazyl, S. P. Kisil', Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 1999. - Vol. 94, N 1. - P11-13 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
R 30 Reactions of 4-hydroxy-5,6,7,8-tetrafluorocoumarin derivatives with S-nucleophiles [Text] / I. T. Bazyl, S. P. Kisil', Ya. V. Burgart, V. I. Saloutin // Journal of Fluorine Chemistry. - 2000. - Vol. 103, № 1. - P3-12 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the reactions with o-aminothiophenol, 4-hydroxy-(3-(imino)acetyl)-5,6,7,8-tetrafluorocoumarins give products of S-substitution at the C-7 atom. 7-Substituted 5,6,8-trifluorocoumarins form benzothiazole as a result of heterocyclic ring opening; 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone undergoes acid splitting to 2-(2-hydroxy-3,4,5,6-tetrafluorophenyl)benzothiazole. Under alkaline conditions, S-substituted coumarins decompose to acetophenone. In an acid medium, 4-hydroxy-3-iminoacetyl-5,6,8-trifluoro-7-(2-aminophenylthio)coumarin affords 7-(2-aminophenylthio)-2-methyl-5,6,8-trifluorochromone. 4-Hydroxy-5,6-difluoro-2-H-pyrano[6,5-a]phenothiazin-2-one was isolated from condensation of 7-(2-aminophenylthio)-4-hydroxy-5,6,8-trifluorocoumarin in the presence of NaH.????Reactions of 3-acetyl(iminoacetyl)-4-hydroxy-5,6,7,8-tetrafluorocoumarins and 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol result in the formation of 5,7,8-trisubstituted derivatives. Interaction of 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol, mercaptoacetic acid and 1,2-ethanedithiol leads to the formation of the 7-substituted products. Acyl-lactone rearrangement of mono- and trisubstituted chromones gives the corresponding coumarins.???? |
F 70 Fluoroaryl containing beta,beta-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones [Text] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2001. - Vol. 108, № 2. - P125-131 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroaryl containing ?,??-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these ?,??-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1,3-butandione???? |
A 10 A route to ethyl alfa-pentafluorobenzoyl-beta-oxobutanoate via its copper(II) chelate [Text] / Ya. V. Burgart, S. P. Kisil', V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2001. - Vol. 11, № 2. - P76 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl 2-pentafluorobenzoyl-3-oxobutanoate has been prepared by the acylation of ethyl acetoacetate with pentafluorobenzoyl chloride via a copper(II) chelate |
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 |
B 33 Bazyl, I. T. Derivatives of 4-hydroxy-5,6,7,8-tetrafluorocoumarin in reactions with o-aminothiophenol [] / I. T. Bazyl, Ya. V. Burgart, S. P. Kisil' // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2000. - Vol. 36, № 6. - С. 904-909 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate [Electronic resource] / S. P. Kisil', M. I. Kodess, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2000. - Vol. 49, № 6. - P1090-1092 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl acetoacetate was acylated with 3,4,5-trifluoro-2,6-dimethoxybenzoyl chloride to give, for the first time, ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate and its copper chelate. The title compound was used for the synthesis of 6,7,8-trifluoro-5-hydroxy-2-methylchromone, 1-(3,4,5-trifluoro-2,6-dimethoxyphenyl)butane-1,3-dione, and its copper chelate \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2000, 49 (6), 1090.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 |