Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins / Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya.,Roeschenthaler Gerd-Volker // TETRAHEDRON. - 2013. - V. 69, l. 29. - P. 5884-5892.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

A three-component reaction of 3-substituted coumarins with N-alkyl-alpha-amino acids and aldehydes gave 1-benzopyrano{[}3,4-c]pyrrolidines as a result of a 1,3-dipolar cycloaddition of an intermediate non-stabilized azomethine ylide at the double bond of the coumarin system in moderate to good yields. In most cases, high regio- and stereo-selectivity of the {[}3+2] cycloaddition was observed. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

3-Substituted coumarins; Nonstabilized azomethine ylide; {[}3+2] cycloaddition; 1-Benzopyrano{[}3,4-c]pyrrolidines; Regioselectivity; Stereoselectivity ALPHA-AMINO-ACIDS; DECARBOXYLATIVE TRANSAMINATION; RECEPTOR ANTAGONISTS; ROUTE; MECHANISM; 5-ARYLOXAZOLIDINES

DOI:

10.1016/j.tet.2013.05.018

Web of Science ID:

ISI:000321316300011

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 22
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ALPHA-AMINO-ACIDS; DECARBOXYLATIVE TRANSAMINATION; RECEPTOR ANTAGONISTS; ROUTE; MECHANISM; 5-ARYLOXAZOLIDINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	RFBR {[}12-03-31036]; DFG {[}RO 362/50/1]
Funding-Text	This work was supported financially by RFBR (Grant 12-03-31036) and DFG RO 362/50/1.
Number-of-Cited-References	24
Usage-Count-Since-2013	24
Journal-ISO	Tetrahedron
Doc-Delivery-Number	176PJ