N 89 Novel fluorinated chromones [Text] / V. I. Saloutin, Z. E. Skryabina, I. T. Bazyl, O. N. Chupakhin // Journal of Fluorine Chemistry. - 1993. - Vol. 65, N 1-2. - P37-41 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The self-condensation of ethyl pentafluorobenzoylacetate leads to the formation of 3-pentafluorophenyl-1H-sopyrono[2,3-b]-6,7,8,9-tetrafluorochrom in 37% yeld. On hydrolysis, this gave 2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone |
A 10 A new approach to the synthesis of fluorinated chromones [Electronic resource] / V. I. Saloutin, I. T. Bazyl, Z. E. Skryabina, V. M. Krokhalev, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1992. - Vol. 41, N 9. - P1714-1715 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The condensation of two molecules of ethyl pentafluorobenzoylacetate gives 1-oxo-3-penta fluorophenyl-1H-pyrano[4,3-b]6,7,8,9-tetrafluorochrome \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1992, 41 (9), 1714.pdf |
S 17 Saloutin, V. I. Condensation of Fluoroalkyl-containing 1,3-Dicarbonyl Compounds with Ethylendiamine [Text] / V. I. Saloutin, Z. E. Skryabina, Ya. V. Burgart // Journal of Fluorine Chemistry. - 1992. - Vol. 56, № 3. - P325-334. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): КОНДЕНСАЦИЯ -- СОЕДИНЕНИЯ ФТОРАЛКИЛСОДЕРЖАЩИЕ -- ФТОРАЛКИЛСОДЕРЖАЩИЕ СОЕДИНЕНИЯ -- СОЕДИНЕНИЯ 1.3-ДИКАРБОНИЛЬНЫЕ -- 1.3-ДИКАРБОНИЛЬНЫЕ СОЕДИНЕНИЯ -- этилендиамины -- ОРГАНИЧЕСКАЯ ХИМИЯ -- ХИМИЯ ОРГАНИЧЕСКАЯ |
C 78 Copper and Copper Oxides Nanopowders in the Oxidative Condensations of Phenylacetylene and Tert-Butylacetylene [Electronic resource] / O. A. Kuznetsova, E. F. Khmara, V. I. Filyakova, M. A. Uimin, A. E. Ermakov, C. K. Rhee, V. N. Charushin // Russian Journal of General Chemistry. - 2007. - Vol. 77, № 3. - P404-408. - Библиогр. : с. 408 (12 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Transformations of phenylacetylene and tert-butylacetylene in the presence of copper and copper oxide (Cusub2/subO, CuO) nanopowders prepared by gas-phase condensation of copper in argon were studied. The reaction of phenylacetylene with copper oxide nanopowders having different phase compositions in the absence of a solvent at room temperature resulted in oxidative condensation of phenylacetylene and complex formation of the condensation product. The complex undergoes decomposition by the action of acids, bases, and compounds capable of forming complexes. According to the X-ray diffraction data, one of the products is a new “parquet” modification of diphenyldiacetylene. Under analogous conditions, tert-butylacetylene gave rise to a complex mixture of products among which di- tert-butyldiacetylene was identified by gas chromatography-mass spectrometry. No copper complexes with the tert-butylacetylene condensation products were detected. \\\\expert2\\nbo\\Russian Journal of General Chemistry\\2007, V. 77, N 3, p.404.pdf |
T 44 The first synthesis of 4-unsubstituted 3-(trifluoroacetyl)coumarins by the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by chromene-coumarin recyclization [Text] / D. L. Chizhov, V. Ya. Sosnovskikh, M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, V. N. Charushin // Synlett. - 2008. - № 2. - P281-285 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\expert2\\nbo\\Synlett\\2008. N 2. P. 281-285.pdf |
R 30 Reaction of Polyhaloalkyl-Substituted Chromones, Pyrones, and Furanones with Salicylaldehydes as a Direct Route to Fused 2H-Chromenes [Electronic resource] / V. Ya. Sosnovskikh, V. Yu. Korotaev, D. L. Chizhov, I. B. Kutyashev, D. S. Yachevskii, O. N. Kazheva, O. A. Dyachenko, V. N. Charushin // Journal of Organic Chemistry. - 2006. - Vol. 71, № 12. - P4538-4543 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyhaloalkyl-substituted chromones, Y-pyrones, and B-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation. ?? \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2006, v.71, N 12, p.4538.pdf |
S 98 Synthesis and antiviral activity of fluorinated pyrido[1,2-a]benzimidazoles [Electronic resource] / S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhnin, O. A. Serova // Pharmaceutical Chemistry Journal. - 2005. - Vol. 39, № 11. - P574-578. - Библиогр. : с. 578 (16 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- ANTIVIRAL ACTIVITY Аннотация: Methods for the synthesis of fluorinated pyrido[1,2-a]benzimidazoles have been developed, and a series of such compounds has been obtained and studied for biological activity. In particular, 5,6-difluoro-2-cyanobenzimidazole (II) was synthesized for the first time using the reaction of 1,2-diamino-4,5-difluorobenzole (I) with cyanoacetic ether. Pyrido[1,2-a]benzimidazoles (III, IV) were obtained via condensation of benzimidazole II with diethylethoxymethylene malonate and ethyl acetoacetate. The synthesized pyrido[1,2-a]benzimidazoles (III–XIII) were subjected to screening on a culture of Vero cells for antiviral activity and cytotoxicity with respect to ortho-poxviruses that are pathogenic for humans. ?? \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2005, 39 (11),574.pdf |
S 53 Shchegol'kov, E. V. The transformations of fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds with methylamine [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, V. I. Saloutin // Journal of Fluorine Chemistry. - 2007. - Vol. 128, № 7. - P779-788 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkylated 1,2,3-triketone 2-arylhydrazones and 2-arylhydrazono-3-oxo esters react variously with methylamine depending on the structure of the fluorinated substituent. 2-Arylhydrazono-1,3-dicarbonyl compounds having "short" fluoroalkyl substituents condense with methylamine at the carbonyl group attached to the non-fluorinated substituent whereas ones containing a lengthy polyfluoroalkyl substituent undergo haloformic cleavage as a result of the amine addition at the carbonyl group bearing such a substituent. The resulting 2-arylazo-3-(N-methyl)amino-1-polyfluoroket-2-en-1-ones and 1-(N-methyl)amino-2-arylhydrazono-3-fluoroalkyl-3-oxopropanamides have complexing properties, and they can bind to nickel(II) and copper(II) ions. Nickel chelates can be obtained by a three-component condensation of 2-arylhydrazono-1,3-dicarbonyl compounds and methylamine in the presence of nickel(II) cations. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2007, v.128. p.779.pdf |
O-57 One-step solvent-free synthesis of fluoroalkyl-substituted 4-hydroxy-2-oxo(thioxo)hexahydropyrimidines in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate [Electronic resource] / E. S. Putilova, N. A. Troitskii, S. G. Zlotin, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 9. - P1392-1395 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient procedure has been developed for the synthesis of fluoroalkyl-substituted 6-aryl-4-hydroxy-2-oxo-(thioxo)hexahydropyrimidine derivatives by three-component condensation of fluorinated ?-dicarbonyl compounds with aromatic aldehydes and urea or thiourea in the absence of a solvent using 6 mol % of 1-butyl-3-methylimidazolium tetrafluoroborate as catalyst. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (9), 1392.pdf |
R 30 Reactions of alkyl 2-benzylidene-2-polyfluoroacylacetates with N,N-dinucleophiles [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1261-1266. - Библиогр. : с. 1266 (16 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Alkyl 2-benzylidene-2-polyfluoroacylacetates react with urea and thiourea to yield 5-ethoxycarbonyl-4-fluoroalkyl-4-hydroxy-6-phenylhexahydropyrimidin-2-ones and -2-thiones and with guanidine sulfate to form 2-amino-5-ethoxycarbonyl-4-fluoroalkyl-6-phenyl-1,6-dihydropyrimidines and 3,6-diethoxycarbonyl-2,7-difluoroalkyl-4,5-diphenyl-4,5-dihydro-1H-pyrido[1,2-a]pyrimidines, and they react with phenylhydrazine to afford 4-alkoxycarbonyl-3-fluoroalkyl-3-hydroxy-1,5-diphenylpyrazolidines. Hydrazine hydrate catalyzes the formation of 3,5-diethoxycarbonyl-2,6-difluoroalkyl-2,6-dihydroxy-4-phenyltetrahydropyrans. When treated with anhydrous hydrazine and o-phenylenediamine, these esters cleave to form the products of condensation of fluoroacyl ester and benzaldehyde with diamines. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1261-1266.pdf |
N 89 Novel polyfluoroalkylated pyrazoles from 2-polyfluoroacylcycloalkanones and hydrazines: Syntheses and unequivocal molecular structure assignment [Text] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich, I. Loop, E. Lork, G. -V. Roeschenthaler // Canadian Journal of Chemistry. - 2001. - Vol. 79, № 2. - P183-194 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDRAZINES -- MOLECULAR STRUCTURE -- ISOMERIC PYRAZOLES; Аннотация: The reaction between 2-trifluoroacetylcycloalkanones and methylhydrazine or phenylhydrazine exclusively yields 3-CF3-pyrazoles. When the chain length of the polyfluorinated substituent in RFC(O) group increases, 5-RF-pyrazoles are isolated. The reaction of 2-trifluoroacetylcyclohexanone with 2-hydrazinopyradine gives 5-hydroxypyrazoline, an intermediate in the formation of 5-CF3-pyrazoles. The regiochemistry of the condensation is probably controlled by the nucleophilicity of the terminal nitrogen in the mono substituted hydrazines and by the steric requirements of the RF group in the 1,3-diketones. Polymethylene chain containing pyrazoles obtained from the 1,3-diketones in question and hydrazine prefer the 3-RF tautomeric form, irrespective of carbocyclic ring size and polyfluoroalkyl group chain length. |
C 73 Condensation of 2-polyfluoroacycloalkanones with aldehydes and dimethylformamide-dimethylacetal [Text] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich, I. Loop, E. Lork, G. -V. Roeschenthaler // Australian Journal of Chemistry. - 2001. - Vol. 54, № 3. - P157-163 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyfluorinated 1,3-diketones containing carbocycles react with aldehydes under Lewis-acid catalysis and also with dimethylformamide-dimetylacetal without catalysis, yielding exclusively (E)-configured condensation products involving the methylene group of the carbocycle. Novel trifluoromethylated chromenes are prepared from 2-trifluoroacetylcycloalkanones and salicylaldehyde. The structures of two new compounds, 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone and 4-trifluoroacetyl-2,3-dihydro-1H-xantene, are confirmed by X-ray structure analysis. |
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.???? |
B 57 Biginelli condensations of fluorinated 3-oxo esters and 1,3-diketones [Text] / V. I. Saloutin, Ya. V. Burgart, O. G. Kuzueva, C. O. Kappe, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2000. - Vol. 103, № 3. - P17-23 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Condensation of fluorinated 3-oxo esters or 1,3-diketones with benzaldehyde and (thio)urea results in the diastereoselective formation of 4-fluoroalkyl-4-hydroxy-2-oxo(thioxo)-6-phenyl-hexahydropyrimidine-5-carboxylates from which by dehydration under acidic conditions the corresponding 6-fluoroalkyl-2-oxo(thioxo)-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates were obtained. Under the same conditions, hexafluoroacetylacetone furnishes 4,6-dihydroxy-4,6-di(trifluoromethyl)-hexahydropyrimidin-2-one. Some further reactions of these pyrimidine derivatives leading to fused heterocycles are described.???? |
S 98 Synthesis of polyfluoroalkyl-containing 1,3,5-triketones [Text] / M. V. Nikonov, D. L. Chizhov, V. G. Ratner, K. I. Pashkevich // Journal of Fluorine Chemistry. - 2000. - Vol. 106, № 2. - P115-116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Synthesis of polyfluoro 1,3,5-triketones by modification of Claisen condensation is described.???? |
P 99 Pyrido[2,3-b]- and pyrimido[4,5-b]quinoxalines: the first fluorine-containing derivatives [Electronic resource] / V. N. Charushin, S. K. Kotovskaya, N. M. Perova, O. N. Chupakhin // Mendeleev Communications. - 2001. - Vol. 11, № 2. - P54-55 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated derivatives of pyrido[2,3-b]- and pyrimido[4,5-b]quinoxalines 5–8 have been prepared through the condensation of 2-amino-3-cyano- and 2-amino-3-aminocarbonyl-substituted 6-fluoro-7-R-quinoxalines 1–4 with dimethyl acetylenedicarboxylate and triethyl orthoformate, respectively?????? \\\\expert2\\nbo\\Mendeleev Communications\\2001, v.11, N 2. p.54.pdf |
S 98 Synthesis of 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone [Text] / D. V. Sevenard, O. Kazakova, D. L. Chizhov, G. -V. Roeschenthaler // Journal of Fluorine Chemistry. - 2006. - Vol. 127, № 7. - P983-986 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A simple, convenient and effective method to synthesize 1,1,1,7,7,7-hexafluoroheptane-2,4,6-trione, the simplest fluorinated 1,3,5-triketone, on a preparative scale was developed. The title compound was obtained by a Claisen-type double condensation of acetone with trifluoroacetic acid ethyl ester and isolated as a solid monohydrate from the reaction mixture. Subsequent dehydration proceeds smoothly to produce the desired compound as an individual substance. Its peculiar tautomeric (keto–enol, ring–chain) features in various solvents are discussed \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2006, v.127, p.983.pdf |
N 76 Non-natural nucleosides based on 1,2,4-triazolo[5,1-c][1,2,4]triazin-4(6H)- ones [Text] / S. L. Deev, T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin // ARKIVOC. - 2009. - Vol. 2009, № 6. - P196-207 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Two regioselective methods for the synthesis of nucleosides in the series of 3-phenyl- and 3- ethoxycarbonyl-1,2,4-triazolo[5,1-c][1,2,4]triazin-4-ones were developed. The first route involves a Vorbruggen glycosylation reaction. The second one is based on condensation of 1,2,4- triazolo[5,1-c][1,2, 4]triazin-4-one sodium salts with protected 1-bromo-sugar derivatives |
F 70 Fluorocontaining 1,3-Dicarbonyl Compounds in the Synthesis of Pyrimidine Derivatives ?? [Electronic resource] / Ya. V. Burgart, O. G. Kuzueva, M. V. Pryadeina, C. O. Kappe, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 6. - P869-880 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Hexafluoroacetylacetone reacts with urea (thiourea) to yield respectively 4,6-bis(hydroxy)-4,6-bis(trifluoromethyl)hexahydropyrimidin-2-one(thione). The dehydration of the products and also reaction of nonsymmetrical fluoroalkyl-containing 1,3-diketones with urea (thiourea) afford substituted pyrimidines. The condensation of fluorinated 3-oxoesters and 1,3-diketones with benzaldehyde and urea (thiourea) results in 5-alkoxycarbonyl(acyl)-4-hydroxy-2-oxo(thioxo)-6-phenyl-4-fluoroalkylhexahydropyrimidines that on dehydration furnish 5-alkoxycarbonyl(acyl)-2-oxo(thioxo)-4-phenyl-6-fluoroalkyltetrahydropyrimidines. Ethyl 7-nonafluorobutyl-5-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-6-carboxylate hydrobromide forms in reaction of dibromoethane with ethyl ether of 2-thioxo-4-phenyl-6-nonafluorobutyltetrahydropyrimidine \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (6), 869.pdf |
S 98 Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl-3-oxopropionates [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, P. A. Slepukhin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 7. - P945-955 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Condensation of ethyl 3-polyfluoroalkyl-3-oxopropionates with excess triethyl orthoformate gave ethyl 3-polyfluoroalkyl-2-ethoxymethylidene-3-oxopropionates which reacted with primary aliphatic, aromatic, and heterocyclic amines to form ethyl 2-alkyl(aryl, hetaryl)aminomethylidene-3-polyfluoroalkyl-3-oxopropionates. According to the X-ray diffraction and IR data, the latter exist in the crystalline state as the corresponding E isomers, while in solution (NMR data), as mixtures of Z and E isomers. Condensation of ethyl 2-ethoxymethylidene-3-oxopropionates with secondary heterocyclic amines (morpholine and pyrrolidine) led to the formation of 2-morpholino(pyrrolidin-1-yl)methylidene-3-fluoroalkyl-3-oxopropionates which were shown to exist as Z isomers both in the crystalline state and in solution \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (7), 945-955.pdf |