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 |
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 |
N 10 N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines [Text] / V. P. Krasnov, G. L. Levit, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2004. - Vol. 15, № 5. - P859-862 : ил. - Библиогр.: с. 862 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC AMINES -- CHLORIDE -- KINETIC RESOLUTION Аннотация: Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine.???? \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2004, v.15, p.859.pdf |
E 54 Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane [Text] / V. P. Krasnov, G. L. Levit, V. N. Charushin, M. I. Kodess, V. N. Kalinin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2002. - Vol. 13, № 16. - P1833-1835. - Bibliogr. : p. 1835 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane were prepared by means of resolution of the racemic mixture via acylation by (S)-naproxen chloride followed by separation and subsequent acid hydrolysis of each of the diastereoisomeric amides. Partial racemization of enantiomeric 3-aminocarboranes was observed during acid hydrolysis \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2002, v.13, p.1833.pdf |
K 46 Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline [Electronic resource] / V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. N. Grishakov, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P27-28 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The acylation of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline by (S)-naproxen acyl chloride resulted in their kinetic resolution with the predominant formation of (S,S)-diastereoisomeric amides (de 78–76%), recrystallisation of which followed by acid hydrolysis gave individual (S)-isomers of heterocyclic amines???? \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 1. p.27.pdf |
K 46 Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine in the reaction with (S)-naproxen chloride: A theoretical study [Electronic resource] / V. A. Potemkin, V. P. Krasnov, G. L. Levit, E. V. Bartashevich, I. N. Andreeva, M. B. Kuzminsky , N. A. Anikin, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2004. - Vol. 14, № 2. - P69-70 : ил. - Библиогр.: с. 70 (14 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): KINETIC RESOLUTION -- CHLORIDE -- COMPUTATION METHODS Аннотация: The kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4- benzoxazine by the action of (S)-naproxen chloride was theoretically studied based on various computation methods. \\\\Expert2\\nbo\\Mendeleev Communications\\2004, v.14, p.69.pdf |
K 46 Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride [Text] / V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Koroleva, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2003. - Vol. 14, № 14. - P1985-1988. - Bibliogr. : p. 1988 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides, des being 80, 66 and 38%, respectively. Recrystallisation of the amides followed by acid hydrolysis gave individual (R)-enantiomers of heterocyclic amines \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2003, v.14, p.1985.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 |
K 46 Kinetic resolution of Heterocyclic Amines using N-Tosyl-(S)-prolyl chloride [Text] : доклад, тезисы доклада / V. N. Charushin, V. P. Krasnov, G. L. Levit, I. N. Andreeva, I. M. Bukrina // XXth European Colloquium on Heterocyclic Chemistry, Stockholm,Sweden, 18-21 Aug. 2002 г. - Stockholm, 2002. - PA:7 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
B 43 Benzimidazo[l,2-a]pyrazolo[l,5-c]quinazoline: a novel heterocyclic system [Electronic resource] / G. N. Lipunova, G. A. Mokrushina, E. B. Granovskaya, O. M. Chasovskikh, V. N. Charushin // Mendeleev Communications. - 1996. - Vol. 6, № 1. - P15-17 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Heating of ethyl 3-[beta-(benzimidazol-2-yl)hydrazine]-2-(polyfluorobenzoyl)acrylates in acetonitrile with potassium fluoride or triethylbenzyl ammonium chloride leads to derivatives of novel heterocyclic systems of benzimidazo[l,2-a]pyrazolo- [1,5-c]quinazoline \\\\expert2\\nbo\\Mendeleev Communications\\1996, v.6, N 1. p.15.pdf |
F 70 Fluorine-Containing Heterocycles. XII. Fluorine-Containing Quinazolin-4-ones and Azolo[a]quinazolinone Derivatives [Electronic resource] / G. N. Lipunova, E. V. Nosova, A. A. Laeva, M. I. Kodess, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 7. - P1071-1080 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Methods for the synthesis of fluorine-containing derivatives of 2-imino-1,3-diphenylquinazolin-4-one, imidazo[1,2-a]quinazolin-5-one, pyrazolo[1,5-a]quinazolin-5-one, and [1,2,4]triazolo[1,5-a]quinazolin-5-one were developed on the basis of the reaction of tetrafluorobenzoyl chloride with N,N?-diphenylguanidine and aminoazoles \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (7), 1071.pdf |
F 70 Fluorine-containing pyrido[1,2-a]quinazolin-6-ones [Electronic resource] / E. V. Nosova, G. N. Lipunova, M. I. Kodess, E. B. Vasil'eva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 10. - P2314-2318 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-aminopyridine and 2-amino-5-methylpyridine with 2,3,4,5-tetrafluorobenzoyl chloride afforded N,N’-diaroylpyridinium salts, which were converted into 6H-pyrido[1,2-a]quinazolin-6-ones by refluxing in toluene in the presence of triethylamine. The angular structure of the tricyclic derivatives obtained was confirmed by 19F and 13C NMR spectroscopy and 2D heteronuclear HetCOR and HMBC experiments \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (10), 2314.pdf |
F 76 Formation of fluoroalkyl-containing pyran-4-one in the reaction of lithium 4,4,4-trifluoro-1-phenylbutane-1,3-dionate with oxalyl chloride [Electronic resource] / O. P. Krasnykh, G. G. Aleksandrov, N. S. Karpenko, V. I. Filyakova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 1. - P178-180 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (1), 178.pdf |
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 |
S 98 Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4- benzotriazines [Электронный ресурс] / S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, O. A. Serova // Pharmaceutical Chemistry Journal. - 2007. - Vol.41, №2. - P62-68 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLIZATION -- CYTOTOXICITY -- FLUORINATION 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 |
2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines [Electronic resource] / E. N. Chulakov, D. A. Gruzdev, G. L. Levit, L. Sh. Sadretdinova, V. P. Krasnov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 948-954. - Bibliogr. : p. 953-954 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): KINETIC RESOLUTION -- ACYL CHLORIDES -- ENANTIOMERS Аннотация: Kinetic resolution of racemic 3 methyl 2,3 dihydro 4H [1,4]benzoxazines in the reaction with chiral 2 arylpropionyl chloride predominantly yielded R*,R* diastereomers. Ibuprofen acyl chloride as acylating agent was found to be more selective and sensitive to the changes in the reaction temperature as compared to naproxen acyl chloride and 2 phenylpropionyl chloride \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 948-954.pdf |
A 10 A new synthetic approach to fused nine-ring systems of the indolo[3,2-b] carbazole family through double Pd-catalyzed intramolecular C-H arylation [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // RSC Advances. - 2016. - Vol. 6, № 74. - С. 70106-70116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IGHT-EMITTING-DIODES -- BIPOLAR HOST MATERIALS -- HOLE-TRANSPORTING MATERIALS Аннотация: A series of new polycyclic compounds bearing the 5,11-dihydroindolo[3,2-b] carbazole ring system, as the common motif of their nine-ring scaffolds, has been successfully prepared with the usage of an efficient two-step strategy, based on the double Friedel-Crafts acylation of 5,11-dihexyl-6,12-di(hetero) aryl-substituted 5,11-dihydroindolo[3,2-b] carbazoles with 2-iodobenzoyl chloride in the presence of SnCl4, followed by regioselective palladium-catalyzed cyclization of the obtained 2,8-bis(2-iodobenzoyl) derivatives into the desired fused 9H-fluoren-9-ones. Some modifications of these nine-ring structures have been performed to afford compounds of the same family bearing the 9H-fluorene fragments. Basic photophysical and electrochemical properties as well as thermal stability of the new fused indolo[3,2-b] carbazole derivatives have been determined. \\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 74. P. 70106.pdf |
A 19 Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride / S. A. Vakarov [и др.] // Tetrahedron: Asymmetry . - 2016. - Vol. 27, № 24. - С. 1231-1237. - Bibliogr. : p. 1236-1237 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC AMINES -- BENZOXAZINES -- 2-METHYLINDOLINE -- KINETIC RESOLUTION Аннотация: The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated. \\\\expert2\\NBO\\Tetrahedron Asymmetry\\2016, v. 27, p.1231.pdf |