1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides / Belskaya Nataliya P.,Lesogorova Svetlana G.,Subbotina Julia O.,Koksharov Aleksandr V.,Slepukhin Pavel A.,Dehaen Wim,Bakulev Vasiliy A. // TETRAHEDRON. - 2015. - V. 71, l. 9. - P. 1438-1447.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo{[}3,4-a]indolizine, octahydropyrrolo{[}3',4':3,4]pyrrolo{[}1,2-a]azepine, hexahydropyrrolo{[}3',41:3,4]pyrrolo{[}2,1-c]{[}1,4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert-cycloallcylamine group and the activity of the azomethine ylides generated. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Diazadiene; S,N-Acetal; Cycloaddition; Maleimide; Azomethine ylide NONSTABILIZED AZOMETHINE YLIDES; FUSED TRICYCLIC AMINES; X=Y-ZH SYSTEMS; DIPOLAR CYCLOADDITION; ONE-POT; DECARBOXYLATIVE ROUTE; POTENTIAL 1,3-DIPOLES; DESILYLATION METHOD; POLYCYCLIC SYSTEMS; CYCLIZATION

DOI:

10.1016/j.tet.2014.12.087

Web of Science ID:

ISI:000350191300009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR 4
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	NONSTABILIZED AZOMETHINE YLIDES; FUSED TRICYCLIC AMINES; X=Y-ZH SYSTEMS; DIPOLAR CYCLOADDITION; ONE-POT; DECARBOXYLATIVE ROUTE; POTENTIAL 1,3-DIPOLES; DESILYLATION METHOD; POLYCYCLIC SYSTEMS; CYCLIZATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	n.p.belskaya@urfu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017 Subbotina, Julia/L-7131-2016
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916 Subbotina, Julia/0000-0002-2227-0787
Number-of-Cited-References	60
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	35
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CC2RC