Title: Synthesis of 7-benzylideneoctahydro-2h-pyrido[1,2-a]pyrazines, bicyclic analogs of the calcium-antagonist flunarizine
Authors: Saleh, Ma ×
Compernolle, Frans
Toppet, Suzanne
Hoornaert, Georges #
Issue Date: Jan-1995
Publisher: Royal soc chemistry
Series Title: Journal of the chemical society-perkin transactions 1 issue:4 pages:369-372
Abstract: The bicyclic amino ketone 4 (2-benzyloctahydro-2H-pyrido[1,2-a]pyrazin-7-one) has been converted in four steps into the pharmacologically interesting (Z)- and (E)-7-benzylideneoctahydro-2H-pyrido[1,2-a]pyrazines 2a, b, bicyclic analogues of the calcium antagonist flunarizine 1. In the key step, olefination of the ketone group, the yield was highly improved (15-20%-->82-85%) by using (a) the phosphonate anion instead of the Wittig reagent and (b) the solvent 1,3-dimethylimidazolidin-2-one instead of tetrahydrofuran. Debenzylation and final substitution of the 2-amino group with (4-FC6H4)(2)CHCl gave the geometric isomers 2a (Z) and 2b (E) in 53% overall yield.
ISSN: 0300-922X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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