Title: Generation of cyclopenta[c]piperidines and pyrrolo[3,4-c]piperidines - Potential substance P antagonists - from adducts of cyclic dienophiles and 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one
Authors: Wu, XJ ×
Toppet, Suzanne
Compernolle, Frans
Hoornaert, GJ #
Issue Date: Jan-2000
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:56 issue:34 pages:6279-6290
Abstract: 1,1,4,4-Tetrasubstituted cyclopenta[c]piperidines and the corresponding 4,4,7,7-pyrrolo[3,4-c]piperidines have been synthesised via cycloaddition of 5-chloro-6-methyl-3-phenyl-2H-1,4-oxazin-2-one with cyclopentene and 3-pyrroline derivatives, respectively, followed by reductive opening of the lactone-bridged adducts. The axial-equatorial conformational preferences of the substituents in these cis-fused bicyclic systems were opposite to those for the monocyclic piperidine analogues. The specific array of functional groups in the bicyclic aminoalcohols was used to accommodate, in stereocontrolled fashion, variable pharmacophoric groups that are of interest for substance P antagonist activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
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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