3-Alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)-acrylonitriles as masked 1,3-dipoles / Belskaya Nataliya P.,Bakulev Vasiliy A.,Deryabina Tatyana G.,Subbotina Julia O.,Kodess Mikhail I.,Dehaen Wim,Toppet Suzanne,Robeyns Koen,Van Meervelt Luc // TETRAHEDRON. - 2009. - V. 65, l. 36. - P. 7662-7672.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Reaction of 3-alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with maleimides, dimethyl maleate and dimethylacetylene dicarboxylate were carried out to give octahydro-pyrrolo{[}3,4-alpha]pyrrolizin-4-ylidenes, hexahydro-pyrrolizines and 6,7-dihydro-5H-pyrrolizines. The formation of the synthesized compounds is explained by a 1,3-dipolar cycloaddition of an in situ generated azomethine ylide. The mechanisms of the formation of these active intermediates were discussed with the aid of density functional theory methods with the B3LYP functional 6-31G(+) calculations using the STAN method and chemical experiments. (C) 2009 Elsevier Ltd. All rights reserved.

Author keywords:

1,2-Diazadiene; Thioaminal; Azomethine ylides; Dipolarophile INTRAMOLECULAR 3+2 CYCLOADDITION; DENSITY-FUNCTIONAL THEORY; AZOMETHINE-YLIDES; AB-INITIO; ONE-POT; PSEUDOPERICYCLIC REACTIONS; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITION; CARBON NANOTUBES; IMINIUM IONS

DOI:

10.1016/j.tet.2009.06.114

Web of Science ID:

ISI:000269340000046

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 5
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	INTRAMOLECULAR 3+2 CYCLOADDITION; DENSITY-FUNCTIONAL THEORY; AZOMETHINE-YLIDES; AB-INITIO; ONE-POT; PSEUDOPERICYCLIC REACTIONS; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITION; CARBON NANOTUBES; IMINIUM IONS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	belska@mail.ustu.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
Funding-Acknowledgement	Russian Foundation for Basic Research {[}RFBR 08-03-00376\_a, RFBR/NNSF 08-03-92208\_a]; Michail-Lomonosov-Forschungsstipendien (DAAD); FWO-Vlaanderen; University of Leuven
Funding-Text	The authors thank the Russian Foundation for Basic Research for financial support (grant RFBR \# 08-03-00376\_a, RFBR/NNSF \# 08-03-92208\_a). J.S. acknowledges Michail-Lomonosov-Forschungsstipendien (DAAD). J.S. is greatly appreciate useful discussion with Prof. R. Herges and F. Koehler (Otto-Diels-Institut fur Organische Chemie, Christian Albrecht University of Kiel, Germany) and their advises about ACID application. We also thank the FWO-Vlaanderen and the University of Leuven for the financial support.
Number-of-Cited-References	86
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	13
Journal-ISO	Tetrahedron
Doc-Delivery-Number	488HM