Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines / Gruzdev D. A.,Levit G. L.,Kodess M. I.,Krasnov V. P. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2012. - V. 48, l. 5. - P. 748-757.

ISSN/EISSN:

0009-3122 / нет данных

Type:

Article

Abstract:

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.

Author keywords:

amides; diastereoisomers; enantiomers; kinetic resolution; nitration; reduction NONENZYMATIC KINETIC RESOLUTION; HETEROCYCLIC AMINES; CHLORIDES; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE

DOI:

10.1007/s10593-012-1053-8

Web of Science ID:

ISI:000308699800009

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	AUG
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	NONENZYMATIC KINETIC RESOLUTION; HETEROCYCLIC AMINES; CHLORIDES; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	ca@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}10-03-00084]; Ural Branch of the Russian Academy of Sciences {[}12-P-3-1030]; Grants Council of the President of the Russian Federation {[}NSh-5505.2012.3]
Funding-Text	The work was financially supported by the Russian Foundation for Basic Research (grant 10-03-00084), Ural Branch of the Russian Academy of Sciences (grant 12-P-3-1030), and also the Grants Council of the President of the Russian Federation (grant NSh-5505.2012.3).
Number-of-Cited-References	34
Usage-Count-Since-2013	6
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	004RW