Title: 3-Alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)-acrylonitriles as masked 1,3-dipoles
Authors: Belskaya, Nataliya P ×
Bakulev, Vasiliy A
Deryabina, Tatyana G
Subbotina, Julia O
Kodess, Mikhail I
Dehaen, Wim
Toppet, Suzanne
Robeyns, Koen
Van Meervelt, Luc #
Issue Date: Sep-2009
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:65 issue:36 pages:7662-7672
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.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Chemistry - miscellaneous
Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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