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 |
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 |
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 |
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 |
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 |
F 70 Fluoro-containing Heterocycles: V. Cyclization of 3-Azolylamino-2-polyfluorobenzoylacrylates [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin, Yu. A. Rozin, O. M. Chasovskikh // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 4. - P570-576 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The heating of ethyl 3-azolylamino-2-polyfluorobenzoylacrylates in acetonitrile in the presence of KF gave rise to derivatives of 1-azolyl-substituted quinolones or azolo[1,5-a]pyrimidines?? \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (4), 570.pdf |
F 70 Fluorine-containing heterocycles. XVI. Reactions of tetrafluorobenzoyl isothiocyanate with hydrazines and their derivatives [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, L. P. Sidorova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 1. - P68-76 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated derivatives of 4H-1,3-benzothiazin-4-one, [1,2,4]triazolo[4,3-a]pyrimidine, [1,2,4]triazolo[3,4-b][1,3]benzazoles, and 1,5-dihydro-1,2,4-triazole-5-thione were synthesized by addition of hydrazines and their derivatives to tetrafluorobenzoyl isothiocyanate, followed by cyclization of intermediate thiosemicarbazides \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (1), 68.pdf |
F 70 Fluoro-containing Heterocycles. IV. Synthesis of Benzimidazole Derivatives [Electronic resource] / S. K. Kotovskaya, N. M. Perova, Z. M. Baskakova, S. A. Romanova, V. N. Charushin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 4. - P564-569 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 2-Mercapto-5,6-difluorobenzimidazole reacts with aliphatic and alicyclic ketones in acetic acid in the presence of catalytic amount of sulfuric acid to afford fluorinated derivatives of 2,3-disubstituted benz[4,5]imidazo[2,1-b][1,3]thiazoles. Reaction with aromatic -haloketones occurs in another way: to furnish 2-phenylacylthio-5,6-difluorobenzimidazoles that in the system acetic anhydride-pyridine undergo cyclization into the corresponding fluorinated derivatives of benz[4,5]imidazo[2,1-b][1,3]thiazoles \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (4), 564.pdf |
M 81 Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, V. I. Filyakova, N. S. Karpenko, D. B. Krivolapov, I. A. Litvinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1272-1278 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN—AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro-1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1272.pdf |
T 82 Transformations of C-adducts of 1,4-diazinium salts with dicarbonyl compounds into polycyclic systems [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 3. - P652-656 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: C-Adducts of 5-(het)aryl-2,3-dicyano-1-pyrazinium salts containing a residue of a 1,3-dicarbonyl compound at position 6 can be involved in the cyclization with hydrazine hydrate giving rise to pyrazino[2,3-c]pyridazines along with the expected pyrazole derivatives. The reactions of the same ?H-adducts with hydroxylamine unexpectedly afforded triazacyclopenta[a]indene derivatives. The crystallographic data on the three-dimensional structures of new polycyclic compounds were obtained \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (3), 652.pdf |
S 69 S-N(H) reactions of 3-fluoronitroarenes with chloromethyl sulfone as the method for the construction of 6-fluoro-3-sulfonylindoles [Electronic resource] / G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 10. - P2048-2053 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5-R-6-Fluoro-3-phenylsulfonylindoles were synthesized by the SN(H) reaction of 3-fluoronitrobenzenes with chloromethyl phenyl sulfone in DMSO in the presence of KOH with subsequent reduction of the nitro group and intramolecular cyclization of imidates \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (10), 2048.pdf |
M 78 Mochul`skaya, N. N. Three-component cyclization of hydroxylamino-substituted quinoline with reactive methylene compounds and formaldehyde: new method for the synthesis of 7-(isoxazolidin-2-yl)-6-fluoroquinolones [Electronic resource] / N. N. Mochul`skaya, L. P. Sidorova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 11. - P2106-2108 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A one-step procedure was developed for the synthesis of new 6-fluoro-7-(isoxazolidin-2-yl)-4-oxo-1,4-dihydroquinolines. The procedure is based on the 1,3-dipolar cycloaddition of the azomethine oxide and 1,1-disubstituted alkenes, which are generated in situ from 6-fluoro-7-hydroxylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and CH-active compounds (dialkyl malonates, ethyl acetoacetate), respectively, in the presence of formaldehyde at 100—120 °C \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (11), 2106.pdf |
S 98 Synthesis of fused quinoxalines [Electronic resource] / M. G. Ponizovskii, A. M. Boguslavskii, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 2. - P68-70 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The intramolecular cyclization of NH and N-alkyl quaternary salts of 2-quinoxaline-2-carboxaldehyde hydrazones affords pyrazolo- [3,4-b]quinoxalines in good yields \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 2. p.68.pdf |
R 30 Reactions of sigma(H)-adducts of 1-ethyl-1,4-diazinium salts with arylalkynes as a one-step approach to pyrrolo[1,2-a]pyrazine derivatives [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1291-1293 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2-a]pyrazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1291-1293.pdf |
F 70 Fluorine-containing quinazolines annulated at the pyrimidine ring [Electronic resource] / E. V. Nosova, A. A. Laeva, T. V. Trashakhova, G. N. Lipunova, P. A. Slepukhin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1303-1308 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorine-containing quinazolines annulated at the sides [a] and [c] were synthesized by the reaction of 2- and 4-hydrazino-substituted quinazolines with aldehydes and subsequent oxidative cyclization. Annulation at the side [b] was performed by alkylation of 2-alkylthio-4(3H)-quinazolinones with bromoethanol and ipso-substitution of the alkylthio group \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1303-1308.pdf |
S 98 Synthesis and antitumor activity of fluorinated derivatives of [i,j]-annelated quinolones [Electronic resource] / G. N. Lipunova, E. V. Nosova, L. P. Sidorova, V. N. Charushin // Pharmaceutical Chemistry Journal. - 2011. - Vol. 45, № 4. - P208-210 : ил. - Bibliogr. : p. 210 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Tri- and pentacyclic fluoroquinolones were synthesized by intramolecular cyclization of the corresponding 3-hydrazinopolyfluorobenzoylacrylates followed by substitution of fluorine atoms by amine residues. The antitumor activity of the resulting compounds was studied at the National Cancer Institute using cultures of 60 cell lines of nine groups, including leukemia, lung tumor, large intestine tumor, CNS tumor, melanoma, ovary tumor, renal tumor, prostate tumor, and breast tumor. Relationships between structure and antitumor activity were analyzed. In vivo experimental data from hollow fiber tests are presented for two derivatives \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2011, 45 (4), 208.pdf |
S 98 Synthesis and tuberculostatic activity of fluoridized 3-Z-hydrazine-2-benzoyl acrylates and their cyclization products / M. A. Kravchenko, E. V. Nosova, G. N. Lipunova, O. M. Chasovskikh, V. A. Sokolov, V. N. Charushin // Problemy tuberkuleza . - 2003. - №7. - С. 49-52 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACRYLIC ACID DERIVATIVE -- PYRAZOLE -- TUBERCULOSTATIC AGENT Аннотация: A rapid development of the resistance of drugs and their toxic and adverse reactions suggest that new antituberculous drugs should be designed. Of the greatest importance is isoniazid resistance. Testing new compounds (IIa, b) has established that the minimum inhibitory concentration of the drug (IIa), 0.39 microgram/ml suppresses the growth of Mycobacterium tuberculosis (MBT) in the macrophages up to 50%, that of the drug (IIb), 1.56 micrograms/ml, causes death in 25% of cases, which is indicative of the high activity of compounds (IIa, b) against MBT |
U 62 Unusual heterocyclization of chalcone podands with 3-amino-1,2,4-triazole / I. G. Ovchinnikova, M. S. Valova, E. G. Matochkina, M. I. Kodess, A. A. Tumashov, P. A. Slepukhin, O. V. Fedorova, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 965-974 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TEMPLATE SYNTHESIS -- CHALCONE PODAND -- CROWN ETHERS Аннотация: A new type of intramolecular cyclization of 1,5-bis[2-(E-3-oxo-3-phenylprop-1-enyl)-phenoxy]-3-oxapentane with 3-aminotriazole promoted by potassium ions was discovered. A cascade mechanism for the formation of crownophane with 4,7-dihydro[1,2,4]triazolo[1,5-a]-pyrimidine fragment was suggested. Effects of oligooxyethylene fragment of the chalcone podand and acid-base catalysis on the selectivity of the cyclocondensation processes and degree of oxidation of triazolopyrimidine fragments were studied. The product structures were confirmed by IR, 1H and 13C NMR spectroscopy and X-ray diffraction study \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 965-974.pdf |