Highly diastereoselective 1,3-dipolar cycloaddition of nonstabilized azomethine ylides to 3-nitro-2-trihalomethyl-2H-chromenes: synthesis of 1-benzopyrano{[}3,4-c]pyrrolidines / Korotaev Vladislav Yu.,Barkov Alexey Yu.,Moshkin Vladimir S.,Matochkina Evgeniya G.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON. - 2013. - V. 69, l. 40. - P. 8602-8608.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-alpha-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano{[}3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the Delta(3)-bond of the chromene system. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2H-chromenes; Nonstabilized azomethine ylides; 1,3-Dipolar cycloaddition; 1-Benzopyrano{[}3,4-c]pyrrolidines 3-NITROCHROMENE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; 3-SUBSTITUTED COUMARINS; RECEPTOR ANTAGONISTS; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 2-PI-COMPONENTS

DOI:

10.1016/j.tet.2013.07.080

Web of Science ID:

ISI:000323873100009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT 7
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	3-NITROCHROMENE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; 3-SUBSTITUTED COUMARINS; RECEPTOR ANTAGONISTS; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 2-PI-COMPONENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016 Moshkin, Vladimir/E-6623-2017
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00126, 12-03-31036]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grants 11-03-00126 and 12-03-31036).
Number-of-Cited-References	34
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	23
Journal-ISO	Tetrahedron
Doc-Delivery-Number	210ZE