С 45 Скрябина, З. Э. Циклизация фторалкилсодержащих 1,3-дикарбонильных соединений с гидроперхлоратом этилендиамина в 1,4 диазепины [] = Cyclization of fluoroalkyl-containing 1,3-dicarbonyl compounds with ethylenediamine hydroperchlorate to 1,4-diazepines / З. Э. Скрябина, Я. В. Бургарт, В. И. Салоутин // Изв. АН СССР. Сер. Химическая. - 1991. - N 4. - С. 890-896 . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
N 71 Nitroalkyl-substituted tetrahydropyrazines in syntheses of azapolycyclic compounds [Electronic resource] / P. A. Slepukhin, N. N. Mochul`skaya, L. P. Sidorova, G. L. Rusinov, M. A. Ezhikova, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 9. - P2197-2203. - Библиогр. : с. 2203 (13 назв. ) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Tri-and tetracyclic compounds were synthesized by the cyclization of 6-alkoxy-2,3-dicyano-5-nitromethyl-1,4,5,6-tetrahydropyrazines with 1,2,3-triazinium and quinoxalinium cations. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (9), 2197-2203.pdf |
S 98 Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4-benzotriazines [Electronic resource] / S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhnin, O. A. Serova // Pharmaceutical Chemistry Journal. - 2007. - Vol. 41, № 2. - P62-68. - Библиогр. : с. 68 (18 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5-diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4-benzotriazine derivatives (Vb-Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses. ?? \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2007, 41 (2), 62.pdf |
A 10 A new approach to fluorinated 4(1H)-quinazolinones [Electronic resource] / A. A. Layeva, E. V. Nosova, G. N. Lipunova, T. V. Trashakhova, V. N. Charushin // Journal of Fluorine Chemistry. - 2007. - Vol. 128, № 7. - P748-754 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new approach for the synthesis of fluorinated 1H-quinazolin-4-ones and 4-substituted quinazolines has been developed. 6-Fluoro-1H-quinazolin-4-ones were obtained by intramolecular cyclization of fluorine-containing S-ethyl N-benzoylisothioureas. Nucleophilic substitution reactions at positions 2 and 7, as well as alkylation at 1-position of quinazolinones were investigated. In addition, the synthesis of fluorine-containing 4-aminoquinazolines was carried out. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2007, v.128. p.748.pdf |
K 66 Kodess, M. I. Reactions of 3-(polyfluoroacyl)chromones with hydroxylamine : synthesis of novel R - containing isoxazole and chromone derivatives [Electronic resource] / M. I. Kodess, V. Ya. Sosnovskikh, V. S. Moshkin // Tetrahedron. - 2008. - Vol. 64, № 34. - P7877-7889 : рис. - Библиогр. : с. 7888-7889 (32 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reaction of 3-(polyfluoroacyl)chromones with hydroxylamine free base proceeds via nucleophilic 1,4-addition followed by opening of the pyrone ring and subsequent cyclization to 4-(polyfluoroalkyl)-4H-chromeno[3,4-d]isoxazol-4-ols in good yields. On treatment with trifluoroacetic acid, the isoxazole ring of this annulated heterocyclic system opens to give 3-cyano-2-(polyfluoroalkyl)chromones, which were successfully hydrolyzed with concentrated H2SO4 to afford 3-carbamoyl-2-(polyfluoroalkyl)chromones. On the other hand, oximation of 3-(polyfluoroacyl)chromones with hydroxylamine hydrochloride occurs either at the carbonyl carbon atom connected to the RF group or at the C-2 atom to give 3-RFC(NOH)-chromones and 5-RF-4-salicyloylisoxazole oximes, respectively. The former were easily converted to 3-RF-4-salicyloylisoxazoles by simple heating in dimethyl sulfoxide.?? \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N34, p. 7877.pdf |
S 98 Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins [Electronic resource] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2005. - Vol. 126, № 6. - P976-983 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23–67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles in the case of o-phenylenediamine and 2-hydroxy-N-perfluoroalkanoylanilines in the case of 2-aminophenol, became the main path of these reactions. Unusual cyclization resulting in 2-pentafluoroethyl-2-pentafluoropropanoylbenzoxazolidine occurs on interaction between dodecafluoro-3,4-epoxyhexane and 2-aminophenol in N,N-dimethylacetamide. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2005, v.126, p.976.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 |
A 10 A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane [Text] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2007. - Vol. 128, № 7. - P769-778 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of octafluoro-2,3-epoxybutane 1 with 2-aminothiophenol gave three kinds of novel fluorocontaining N,S-heterocyclic compounds depending on the solvent nature: 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 2, 2-trifluoromethyl-2-[1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-benzothiazolidine 6 and 5a,11a-bis(trifluoromethyl)-5a,6,11a,12-tetrahydro-5,11-dithia-6,12-diazanaphthacene 5. Use of the toluene, dioxane, tetrahydrofuran, acetonitrile and dimethoxyethane gave the unexpected dihydrobenzothiazine 2 (RS,SR RR,SS) in good to moderate yields. In dimethylsulfoxide and N,N-dimethylacetamide, unusual cyclization occurred resulting in benzothiazolidine 6 (RS,SR/RR,SS 1:1) in moderate yields. Formation of minor 1,1,1,3,4,4,4-heptafluoro-3-(2-aminophenylthio)-2,2-dihydroxybutane 4 which was converted into bis(benzothiazine) 5 was observed in all solvents tested with the exception of toluene and dioxane. The molecular structure of the RS,SR-diastereomer of dihydrobenzothiazine 2, bis(benzothiazine) 5 and the RS,SR-diastereomer of benzothiazolidine 6 has been established by X-ray crystallography. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2007, v.128. p.769.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 |
S 98 Synthesis of mesoionic[1,2,3]triazolo[5,1-delta][1,2,5]triazepines [Text] / E. A. Savel'eva, Yu. A. Rozin, M. I. Kodess, L. V. Meervelt, W. Dehaen, Yu. Yu. Morzherin, V. A. Bakulev // Tetrahedron. - 2004. - Vol. 60, № 25. - P5367-5372 : ил. - Библиогр.: с. 5371-5372 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZOLIUM -- SYNTHESIS -- CARBONYL GROUP Аннотация: Intramolecular cyclization of 1-amino-3-phenacyl-4-carbohydrazido-1,2,3-triazolium-5-olates has been shown to take place via selective interaction of the carbonyl group with the terminal amino function of the hydrazido group to form a 1,2,5-triazepine ring. Minor products, resulting from the interaction of the ?-nitrogen atom of the hydrazido group with the carbonyl function, having a N-amino-pyridazine structure were also detected and isolated. A general method for the synthesis of novel mesoionic 2-amino-7-aryl-4-oxo-2,4,5,8-tetrahydro[1,2,3]triazolo[5,1-d][1,2,5]triazepin-9-ium-3-olates was developed. \\\\Expert2\\nbo\\Tetrahedron\\2004, v.60, p.5367.pdf |
A 10 A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem AN-SNipso and SNH-SNipso reactions [Text] / O. N. Chupakhin, G. L. Rusinov, D. G. Beresnev, V. N. Charushin, H. Neunhoeffer // Journal of Heterocyclic Chemistry. - 2001. - Т. 38, № 4. - P901-907 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new synthetic approach to condensed 1,2,4-triazines based on using the tandem AN-SNipso and SNH-SNipso reactions has been developed. 5-Methoxy-3-penyl-l,2,4 1,2,4-triazine and its N1-methyl quaternary salt were found to react with C,N-, C,O- and N,N?-bifunctional nucleophiles (m-phenylenediamine, resorcinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products. \\\\Cserver\\dist\\НБО\\Электронная библиотека_Библиогр1\\Journal of Heterocyclic Chemistry\\2001.v.38.p.901.Chupachin.pdf |
R 30 Reaction of 5-halo-1,2,3-thiadiazoles with aliphatic diamines. Synthesis and intramolecular cyclization of bis(1,2,3-triazolyl-1,2,3-thiadiazolyl)sulfides [Text] / N. N. Volkova, E. V. Tarasov, M. I. Kodess, L. Van Meerlent, W. Dehaen, V. A. Bakulev // Organic and Biomolecular Chemistry. - 2003. - Vol. 1, № 22. - P4030-4038 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Bis[1,2,3]triazolo[1,5-f:5?,1?-b][1,3,6]thiadiazepine and [1,5-g:5?,1?-b][1,3,7]thiadiazocine ring systems have been synthesized from 5-halo-1,2,3-thiadiazoles and aliphatic diamines. We have found that the last step of the process is the cyclization of initially formed bis(1,2,3-triazolyl-1,2,3-thiadiazolyl)sulfides. The structures of the intermediates and products were supported by different NMR spectroscopic methods (1H coupled 13C NMR, 2D HETCOR, HMBC and 1D INADEQUATE experiments) and mass spectrometry. Differences in the reaction pathway for aliphatic and less nucleophilic aromatic diamines were determined. |
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???? |
U 88 Use of tandem AN-AN reactions for the synthesis of thiazolo[4,5-e]-1,2,4-triazines [Electronic resource] / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P28-29 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Aryl-1,2,4-triazines react with thioamides in acetic anhydride to produce thiazolo[4,5-e]-1,2,4-triazine derivatives and this reaction represents a new method for the fusion of thiazole and 1,2,4-triazine rings based on the nucleophilic ortho-diaddition type (AN-AN) cyclization reactions?????? \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 1. p.28.pdf |
S 73 Sosnovskikh, V. Ya. One-pot three-component reaction of 3-(polyfluoroacyl)chromones with active methylene compounds and ammonium acetate: regioselective synthesis of novel RF-containing nicotinic acid derivatives [Text] / V. Ya. Sosnovskikh, R. A. Irgashev, M. I. Kodess // Tetrahedron. - 2008. - Vol. 64, № 13. - P2997-3004 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THREE-COMPONENT REACTIONS -- AMMONIUM ACETATE Аннотация: Reactions of 3-(polyfluoroacyl)chromones with acetoacetamide and ethyl acetoacetate in the presence of ammonium acetate proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent cyclization to 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinamides, ethyl 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinates, and ethyl 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carboxylates. Similar reaction with ?-aminocrotononitrile gave 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles???? \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N13, p. 2997.pdf |
S 98 Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins [Text] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2009. - Vol. 130, № 10. - P853-860 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OXIDES OF INTERNAL PERFLUOROOLEFINS -- 1,5-bIS(PERFLUOROALKYL)TETRAAZABICYCLO[3.3.0]OCTANE-3,7-D Аннотация: The reaction of oxides of internal perfluoroolefins 1–3 with urea gave two kinds of novel fluorine containing N-heterocyclic compounds depending on the solvent nature: 1,5-bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones 4a–c and 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols 7a–d. Use of polar dimethylsulfoxide, N,N-dimethylacetamide and acetonitrile afforded glycolurils 4a–c in moderate yields. In dioxane, unexpected cyclization occurred resulting in oxazolines 7a–d in high yields. A similar reaction of oxiranes 2, 3 with urea in aqueous dioxane gave mixtures of 4,5-dihydroxy-4,5-bis(perfluoroalkyl)imidazolidine-2-ones 9b, c, glycolurils 4b, c and oxazolines 7b–d. The molecular structure of trans-isomers of oxazoline 7b and imidazolidine 9b has been established by X-ray crystallography?? \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2009, V. 130, P. 853.pdf |
U 62 Unusual transformation of a fluoroalkyl-containing beta-aminovinyl ketone [Electronic resource] / O. P. Krasnykh, N. S. Karpenko, V. I. Filyakova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1355-1356 : ил. - Библиогр.: с. 1356 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHLORIDE -- KETONE DERIVATIVE -- CYCLIZATION -- FLUOROALKYL-CONTAINING BETA-AMINOVINYL KETONE \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1355.pdf |
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 |
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 |