K 46 Kinetic resolution of (+/-)-2,3-dihydro-3-methyl-4H-1,4-benzoxazines with (S)-naproxen [Text] / V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Koroleva, M. I. Kodess, O. N. Chupakhin, M. N. Kim, H. S. Lee, Y. J. Park, K. -C. Kim> // Tetrahedron: Asymmetry . - 1999. - Vol. 10, N 14. - P2691-2702 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
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 |
F 70 Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles [Electronic resource] / A. A. Layeva, E. V. Nosova, G. N. Lipunova, V. N. Charushin> // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 5. - P947-984 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Methods for the synthesis of fluoro-containing benzazoles and benzazines from fluoroarenes (fluoroanilines, fluorobenzoic acids, fluoroacetophenones, fluorophenols, etc.) are described. The potentialities of the most important synthons are considered. Ways of constructing hetero- cycles with fluorine atoms in the annulated benzene fragment are discussed \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (5), 947.pdf |
K 46 Kinetic resolution of (±)-2,3-dihydro-3-methyl-4h-1,4-benzoxazines with (s)-naproxen / V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Koroleva, M. I. Kodess, O. N. Chupakhin, M. N. Kim, H. S. Lee, Y. J. Park, K. -C. Kim> // Tetrahedron: Asymmetry . - 1999. - Vol. 10, № 14. - С. 2691-2702. - Bibliogr. : p. 2702 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ENANTIOMERS -- BENZOXAZINES -- ACYL CHLORIDES \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\1999. v. 10. p.2691.pdf |
A 10 A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines [Electronic resource] / D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov> // Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246. - Bibliogr. : p. 1246 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): RACEMIC FLUORINATED -- 1,2,3,4-TETRAHYDROQUINOLINES -- BENZOXAZINES Аннотация: The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99%) was developed \\\\expert2\\NBO\\Tetrahedron Asymmetry\\2013, in Press, Corr. Proof, 4 Sept.pdf |
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 |
C 51 Chemoenzymic arabinosylation of 2-aminopurine bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines [Electronic resource] / B. Z. Eletskaya, I. D. Konstantinova, A. S. Paramonov, S. E. Esipov, D. A. Gruzdev, A. Yu. Vigorov, G. L. Levit, A. I. Miroshnikov, V. P. Krasnov, V. N. Charushin> // Mendeleev Communications. - 2016. - Vol. 26, № 1. - С. 6-8 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PURINE NUCLEOSIDE PHOSPHORYLASE -- 2-AMINOPURINE CONJUGATES Аннотация: Chemoenzymic transglycosylation of 2-aminopurine conjugates with enantiomerically pure 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines under the action of recombinant E. coli purine nucleoside phosphorylase afforded the corresponding arabinofuranosides, yields of the target compds. being dependent on both the structure and configuration of the fragment of heterocyclic amine attached at C-6 position of purine moiety. \\\\expert2\\nbo\\Mendeleev Communications\\2016, v.26, p. 6-8.pdf |
D 53 Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides / S. A. Vakarov, D. A. Gruzdev, L. Sh. Sadretdinova, E. N. Chulakov, M. G. Pervova, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. P. Krasnov> // Tetrahedron: Asymmetry . - 2015. - Vol. 26, № 5-6. - С. 312-319 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBONYL CHLORIDES -- DIASTEREOSELECTIVE SYNTHESIS -- dIASTEREOSELECTIVE ACYLATION \\\\expert2\\NBO\\Tetrahedron Asymmetry\\2015, v. 26, p.312.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 |
Mutual kinetic resolution of 3-methyl-3,4-dihydro-2h-1,4-benzoxazines and 2-alkoxyacyl chlorides / S. A. Vakarov, D. Gruzdev, L. S. Sadretdinova, M. I. Kodess, A. A. Tumashov, E. B. Gorbunov, G. L. Levit, V. P. Krasnov> // Chemistry of Heterocyclic Compounds. - 2018. - Vol. 54, № 4. - P437-446 Рубрики: ХИМИЧЕСКИЕ НАУКИ |