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, (±)-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 |
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 |
K 46 Kinetic resolution of (+-)-2-methyl-1,2,3,4-tetrahydroquinoline by proline derivatives [Text] : доклад, тезисы доклада / V. P. Krasnov, I. A. Nizova, A. Yu. Vigorov, G. L. Levit, L. Sh. Sadretdinova, V. N. Charushin // 15th European Symposium on Organic Chemistry, Dublin, 8-13 July 2007 :abstr. - Dublin, Ireland, 2007. - 231 (P167) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 91 Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides [Text] / G. L. Levit, D. A. Gruzdev, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2011. - Vol. 22, № 2. - P185-189. - Bibliogr. : p. 189 (17ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe H NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2011, v. 22, p.185.pdf |
S 98 Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines / D. A. Gruzdev, G. L. Levit, M. I. Kodess, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №5. - С. 748-757 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AMIDES -- DIASTEREOISOMERS -- ENANTIOMERS Аннотация: Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro compound followed by the reduction led to (S)-6-amino-2-methyl-1-trifluoroacetyl-1,2,3,4-tetra-hydroquinoline in a high yield \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 5, p.748-757.pdf |
S 98 Synthesis of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids / D. A. Rudenko, S. N. Shurov, M. I. Kodess, M. A. Ezhikova, A. N. Vasyanin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2012. - Vol.48, №6. - С. 799-803 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- TETRAHYDROQUINOLINE -- CARBOXYLIC ACIDS Аннотация: 2-Substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids were synthesized by reaction of acyl- and aroylpyruvic acids with 3-amino-5,5-dimethylcyclohex-2-en-1-one. A plausible mechanism of their formation was proposed on the basis of ab initio quantum-chemical calculations \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2012, 48 (6), 799-803.pdf |
S 98 Synthesis of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]oxazino[5,4,3-de]quinolin-3-ones [Electronic resource] / D. A. Rudenko, P. A. Slepukhin, V. I. Karmanov, M. I. Vakhrin, S. N. Shurov, Yu. A. Shchurov // Chemistry of Heterocyclic Compounds. - 2013. - Vol.48, №10. - 1539-1544. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDROXYLAMINE -- QUANTUM-CHEMICAL CALCULATIONS -- TETRAHYDROQUINOLINE-4-CARBOXYLIC ACIDS Аннотация: The reaction of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydroxylamine results in the formation of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]ox-azino[5,4,3-de]quinolin-3-ones. The structure of the 5-phenyl derivative has been established by X-ray structural analysis. A possible mechanism of the reaction has been proposed on the basis of nonempirical quantum-chemical calculations \\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.48, N 10, p. 1539-1544.pdf |
S 98 Synthesis and the molecular and crystal structures of methyl 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylates [Electronic resource] / D. A. Rudenko, M. V. Artemova, P. A. Slepukhin, V. I. Karmanov, S. N. Shurov // Chemistry of Heterocyclic Compounds. - 2013. - Vol.48, №9. - P1321-1324 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- MOLECULAR STRUCTURE -- CRYSTAL STRUCTURE Аннотация: Methyl 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylates were obtained as a result of 3-amino-5,5-dimethylcyclohex-2-enone reaction with the methyl esters of acyl(aroyl)pyruvic acids. The structure of methyl 7,7-dimethyl-5-oxo-2-phenyl-5,6,7,8-tetrahydroquinoline-4-carboxylate was established by X-ray structural analysis \\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.48, N 9, p. 1321-1324.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 |
G 90 Gruzdev, D. A. Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains / D. A. Gruzdev, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2012. - Vol.23. - С. 1640-1646. - Bibliogr.: p. 1645-1646 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC AMINES -- RACEMIC AMINES -- ACYL CHLORIDES Аннотация: A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee >99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride \\\\expert2\\NBO\\Tetrahedron Asymmetry\\2012, v. 23, p.1640.pdf |
S 98 Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment [Electronic resource] / E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2015. - Vol. 25. - С. 412-414. - Bibliogr. : p. 414 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2-AMINOPURINE -- PURIN-6-YL -- HETEROCYCLIC AMINES Аннотация: Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro- 2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6- hexanoic acid with nitrogen heterocycles were used. \\\\expert2\\nbo\\Mendeleev Communications\\2015, v.25, p. 412.pdf |
K 46 Kinetic resolution of racemic 6-substituted 1,2,3,4-tetrahydroquinaldines with chiral acyl chlorides. Experiment and quantum chemical simulation / E. N. Chulakov, M. A. Korolyova, L. S. Sadretdinova [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 5. - P890-899 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A comparative study of the kinetic resolution (KR) of racemic 6-substituted 2-methyl-1,2,3,4-tetrahydroquinolines with acyl chlorides of (S)-naproxen, N-phthaloyl-(S)-leucine, and (R)-O-phenyllactic acid was carried out. The selectivity factors in the KR of racemic amines with acyl chlorides of (S)-naproxen and (R)-O-phenyllactic acid were shown to be approximately the same and higher than those for the KR of N-phthaloyl-(S)-leucyl chloride. The reasons for the stereodifferentiation in the KR of racemic tetrahydroquinaldines containing groups of different electronic properties by acyl chlorides of three different chiral acids were explained using the DFT method. The conditions for stabilizing π—π interactions of aromatic fragments of the reagents, which do not occur in the same form in the transition state and lead to the minor diastereoisomeric product, are created in the transition state of the faster acylation reaction with (S)-naproxen and (R)-O-phenyllactic acyl chlorides. In the case of the KR of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline with N-phthaloyl-(S)-leucyl chloride, the acylation diastereoselectivity is determined, most likely, by conformational factors. The individual (S)-enantiomer of 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline of high optical purity was synthesized using the KR of the racemate with (S)-naproxen acyl chloride. |