Kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and its structural analogs by using 2-arylpropionyl chlorides / Chulakov E. N.,Levit G. L.,Tumashov A. A.,Sadretdinova L. Sh.,Krasnov V. P. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2012. - V. 48, l. 5. - P. 724-732.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

Acylation of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with the acyl chlorides of naproxen, ibuprofen, and 2-phenylpropionic acid has been found to lead to efficient kinetic resolution with predominant formation of the (S,S)-(R,R)-diastereoisomers. The highest acylation stereoselectivity was found in toluene at -20A degrees C. No significant kinetic resolution of N-(sec-butyl)aniline and 2-methylpiperidine was achieved by using 2-arylpropionyl chlorides.

Author keywords:

2-arylpropionic acids; 2-methylindoline; 2-methyl-1,2,3,4-tetrahydroquinoline; acyl chlorides; acylation; kinetic resolution HETEROCYCLIC AMINES; CARBOXYLIC-ACIDS; ACYL TRANSFER; ESTERS; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; DIASTEREOSELECTIVITY; AGENT

DOI:

10.1007/s10593-012-1051-x

Web of Science ID:

ISI:000308699800007

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
EISSN	1573-8353
Keywords-Plus	HETEROCYCLIC AMINES; CARBOXYLIC-ACIDS; ACYL TRANSFER; ESTERS; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; DIASTEREOSELECTIVITY; AGENT
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 Russian Federation President {[}NSh-5505.2012.3]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (grant 10-03-00084), Ural Branch of the Russian Academy of Sciences (project 12-P-3-1030), and the Grants Council of the Russian Federation President (grant NSh-5505.2012.3).
Number-of-Cited-References	29
Usage-Count-Since-2013	4
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	004RW