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Title: Diels-Alder reactions of pyridine o-quinodimethane analogues generated from functionalised o-bis(chloromethyl)pyridines
Authors: Carly, PR ×
Cappelle, SL
Compernolle, Frans
Hoornaert, Georges #
Issue Date: Jan-1996
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:52 issue:36 pages:11889-11904
Abstract: The polyfunctional 2,3- and 3,4-o-bis(chloromethyl)pyridines 3, produced vip cycloaddition of the oxazinones 2 with propargyl chloride and 1,4-dichloro-2-butyne, were used as precursors of various pyridine o-quinodimethane analogues. The 2,3- and 3,4-dimethylenepyridine systems were generated via reductive 1,4-elimination with iodide and trapped in situ with various dienophiles to form the tetrahydroquinoline and -isoquinoline type adducts. A regiospecific cycloaddition was observed for the 3,4-dimethylenepyridine system with electron-rich dienophiles, i.e. dihydrofuran and ethyl vinyl ether, in contrast to the reaction with methyl acrylate. Copyright (C) 1996 Elsevier Science Ltd.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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