П 50 Полифторбензоилхлориды и изотиоцианаты в реакциях с СH-активными бензимидазолами [] = Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles / Э. В. Носова, Г. Н. Липунова, А. А. Лаева, В. Н. Чарушин // Изв. АН. Сер. Химическая. - 2005. - N 3. - 720-724: рис. - Библиогр. : с. 724 (24 назв.) . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Взаимодействием (2-бензоилметил)бензимидазола с тетра- и пентафторбензоилхлоридами получены фторсодержащие 6-бензоил-7H-бензимидазо[3,2-а]хинолоны. На основе 2-цианометилбензимидазола или 2-бензоилметилбензимидазола и тетра(пента)фторбензоилизотиоцианатов синтезированы фторсодержащие 1,3-бензотиазиноны, для которых выявлены различия в реакциях с циклоалкилиминами. |
F 70 Fluoro-containing heterocycles: Part XIII. Fluoro-containing derivatives of thiazolo[3,2-a]-, benzothiazolo[3,2-a]-, and benzimidazo[3,2-a]quinazolinones [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 11. - P1671-1677. - Библиогр. : с. 1677 (22 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-aminothiazole, derivatives of 2-aminobenzothiazole and 2-aminobenzoimidazole with polyfluorobenzoyl chlorides gave rise to acylation products that at heating in the diphenyl ether formed fluoro-containing derivatives of thiazolo[3,2- a]-, benzothiazolo[3,2- a]-, and benzimidazo[3,2- a]quinazolinone. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (11), 1671.pdf |
K 46 Kinetic resolution of 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes via acylation with chiral acyl chlorides [Electronic resource] / G. L. Levit, V. P. Krasnov, A. M. Demin, M. I. Kodess, L. Sh. Sadretdinova, T. V. Matveeva, V. A. Ol'shevskaya, V. N. Kalinin, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2004. - Vol. 14, № 6. - P293-295 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A study of the kinetic resolution of racemic 1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes by chiral acyl chlorides has shown that N-tosyl-(S)-prolyl and N-phthaloyl-(S)-alaninyl chlorides are more efficient resolving agents than (S)-naproxen chloride. \\\\Expert2\\nbo\\Mendeleev Communications\\2004, v.14, p.293.pdf |
S 98 Synthesis and the reactions of trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines [Electronic resource] / O. G. Khudina, E. V. Shchegol'kov, Ya. V. Burgart, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, O. A. Dyachenko, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2005. - Vol. 126, № 8. - P1230-1238 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The coupling of trifluoromethylated 1,3-diketones with (het)aryldiazonium chlorides results mainly in the formation of 1,2,3-triketones 2-(het)arylhydrazones while using hetarylamine with a NH-group at the ?-position of the heterocycle as the diazonium component gives 4,7-dihydroazolo[5,1-c]triazines due to cyclization at the trifluoroacetyl fragment. Trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 7-hydroxy-4,7-dihydroazolo[5,1-c]triazines react regio-selectively with methyl hydrazine and phenyl hydrazine to form 3-CF3-pyrazoles. The long-range coupling constants (JF-H) of 1-methylpyrazoles and the chemical shifts of trifluoromethyl groups in the 19F NMR spectra can be used for the determination of regio-isomeric structures of mono(trifluoromethyl)-substituted pyrazoles. 2-(Het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines with two trifluoromethyl substituents afford the mixtures of cis- and trans-azopyrazoles in the reactions with hydrazines. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2005, v.126, p.1230.pdf |
N 85 Nosova, E. V. Cyclization of 2-halobenzoyl chlorides with dinucleophiles as a versatile approach to fused heterocycles [Electronic resource] / E. V. Nosova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1137-1152 : рис. - Библиогр.: с. 1151-1152 (103 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The review surveys methods for the construction of bi- and polycyclic nitrogen-, oxygen-, and sulfur-containing heterocycles based on reactions of 2-halobenzoyl chlorides with dinucleophiles.?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1137.pdf |
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???? |
C 47 Charushin, V. N. Fluorinated derivatives of condensed heterocycles on the basis of (polyfluorobenzoyl)chlorides [Text] : доклад, тезисы доклада / V. N. Charushin, E. V. Nosova, G. N. Lipunova // XXth European Colloquium on Heterocyclic Chemistry, Stockholm,Sweden, 18-21 Aug. 2002 г. - Stockholm, 2002. - PB:4 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of fluorinated 2(3)-arylhydrazones of 1,2,3-tri(1,2,3,4-tetra)carbonyl compounds and their heterocyclization reactions [] / Ya. V. Burgart, A. S. Fokin, O. G. Kuzueva, O. N. Chupakhin, V. I. Saloutin // Journal of Fluorine Chemistry. - 1998. - Vol. 92, № 2. - С. 101-108 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-triketones, 2-arylhydrazone-1,2,3-diketo esters and 3-arylhydrazone-1,2,3,4-triketo esters have been prepared by the coupling of fluorine-containing 1,3-keto esters, 1,3-diketones, acyl(aroyl)pyruvic esters and their chelates with aryldiazonium chlorides. The arylhydrazones react with hydrazine hydrate, phenylhydrazine, thiosemicarbazide and hydroxylamine to form the corresponding pyrazole and isoxazole derivatives. Interaction of 3-arylhydrazone-1,2,3,4-diketo esters with o-phenylenediamine results in quinoxaline products. Intramolecular cyclization of the arylhydrazones with pentafluorophenyl substituents leads to cinnolone derivatives |
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 |
K 96 Kuzueva, O. G. Synthesis of 2-arylhydrazones of aliphatic fluorine-containing 1,2,3-tricarbonyl compounds and their reactions with dinucleophiles [Electronic resource] / O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1998. - Vol. 47, № 4. - P673-678 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-tricarbonyl compounds were obtained by coupling fluorine-containing 3-oxo esters, 1,3-diketones, and their copper chelates with aryldiazonium chlorides. Reactions of these arylhydrazones with hydrazine hydrate, phenylhydrazine, thiosemicarbazide, and hydroxylamine gave the corresponding pyrazole and isoxazole derivatives \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1998, 47 (4), 673.pdf |
S 98 Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2584-2590 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkyl-containing 1,2,3-triketone 2-(2,3-dimethyl-5-oxo-1-phenyl-1,2-dihydropyrazol-4-yl)-, 2-(4-ethoxycarbonylpyrazol-3-yl)-, and 2-(1,2,4-triazol-3-yl)hydrazones were synthesized by the azo coupling reactions of fluorinated 1,3-diketones with the corresponding hetaryldiazonium chlorides. The hetarylhydrazones thus synthesized were subjected to cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to give 3-fluoroalkyl-4-hetarylazopyrazoles \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2584-2590.pdf |
F 70 Fluorine-containing Heterocycles. X. Acetoacetamides in the Synthesis of Fluorine-containing Chromone [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 8. - P1162-1166 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorine-containing chromone-3-carboxamides were synthesized by reaction of tetra(penta)fluoro-benzoyl chlorides with acetoacetamides in dichloromethane in the presence of triethylamine. Nucleophilic substitution of fluorine atoms by amine rests in compounds synthesized was investigated \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (8), 1162.pdf |
F 70 Fluorocontaining Heterocycles: IX. Derivatives of Imidazo[2,1-b][1,3]benzothiazine [Electronic resource] / G. N. Lipunova, E. V. Nosova, G. A. Mokrushina, E. G. Oglobina, G. G. Aleksandrov, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2003. - Vol. 39, № 2. - P248-256 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The heating of derivatives of benzimidazole-2-thione and imidazolidine-2-thione with tetra(penta)fluorobenzoyl chlorides in toluene or pyridine gave rise to fluorocontaining derivatives of imidazo[2,1-b][1,3]benzothiazine. The latter were studied in reactions of nucleophilic substitution of fluorine for amino groups \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2003, 39 (2), 248.pdf |
F 70 Fluorinated benzimidazo[1,2-a]quinolones [Electronic resource] / G. N. Lipunova, E. V. Nosova, E. B. Vasil'eva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 2. - P457-460 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 2-cyanomethylbenzimidazole with polyfluorobenzoyl chlorides afforded 2-(1,3-dihydrobenzimidazol-2-ylidene)-3-oxo-3-polyfluorophenylpropionitriles. Refluxing of the latter compounds in acetonitrile in the presence of DBU or in dimethylformamide in the presence of amines gave rise to fluorine-containing derivatives of benzimidazo[1,2-a]quinolone?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (2), 457.pdf |
K 46 Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine [Electronic resource] / V. P. Krasnov, G. L. Levit, M. A. Koroleva, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1253-1256 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl-(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1253.pdf |
S 98 Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones [Electronic resource] / A. A. Layeva, E. V. Nosova, G. N. Lipunova, T. V. Trashakhova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 9. - P1821-1827 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5-Fluoroquinazoline-2,4-diones and their 2-thio analogs were obtained from 6-fluoroanthranilic acid. Two convenient routes to 5-fluoroquinazolin-4-ones involved cyclocondensation of 6-fluoroanthranilamide with acid chlorides (anhydrides) or with aromatic (heterocyclic) aldehydes. A method for the synthesis of 7-fluoroquinazolin-4-one from 2,4-difluorobenzoic acid was proposed \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (9), 1821.pdf |
P 80 Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 3. - P733-737 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-benzoylmethylbenzimidazole with tetra- and pentafluorobenzoyl chlorides afford fluorine-containing 6-benzoyl-7H-benzimidazo[3,2-a]quinolones. 2-Cyanomethyl- or 2-benzoylmethylbenzimidazole reacts with tetra(penta) fluorobenzoyl isothiocyanates to give fluorine containing 1,3-benzothiazinones, which differently behave in reactions with cycloalkylimines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (3), 733.pdf |
A 53 An efficient synthesis of alkylfluoroalkylketones [Text] / O. G. Khomutov, V. I. Filyakova, A. V. Kutchin, K. I. Pashkevich // Journal of Fluorine Chemistry. - 1992. - Vol. 58, № 2-3. - P161 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Interaction of fluoroacyl chlorides with lithium tetraalkylaluminates II prepared by the hydroalumination of alkenes I results in fluorinated ketones III with yields of 65–70%.??RF = CF3, H(CF2)2, C4F9, C6F13 R1 = C3H7, C4H9, C6H13, C7H15??The reaction is simple and does not require an argon atmosphere, as is needed for most reactions of organoaluminum compounds???? |
A 19 Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides [Text] / D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2010. - Vol. 21, № 8. - P936-942 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2010, v. 21, p.936.pdf |
A 89 Asymmetric induction in the reactions of azinones with C-nucleophiles [Electronic resource] / O. N. Chupakhin, I. N. Egorov, V. L. Rusinov, P. A. Slepukhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 5. - P991-1001 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINONES -- QUINOXALIN -- C-NUCLEOPHILES -- INDOLES Аннотация: Effect of acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (5), 991-1001.pdf |