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Title: Synthesis and 2,7-functionalization of the bicyclic lactam 2-benzyloctahydropyrido[1,2-a]pyrazin-6-one
Authors: Saleh, Ma ×
Compernolle, Frans
Vandenbranden, S
Debuysser, W
Hoornaert, Georges #
Issue Date: Jan-1993
Publisher: Amer chemical soc
Series Title: Journal of Organic Chemistry vol:58 issue:3 pages:690-695
Abstract: This report describes the synthesis of the title compound 7 and its conversion into 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines, i.e., bicyclic analogues of the monocyclic piperazine drug lidoflazine. The synthesis of 7 is based on a 3-fold amino substitution of methyl 6-chlor-5-oxohexanoate (12), initiated by displacement of chlorine with N-benzyl-N'-trityl-1,2-ethanediamine. The required trielectrophile 12 was prepared readily from commercially available diethyl 2-acetyl-glutarate. The 7-position of compound 7 was functionalized through reaction of the lactam anion with benzophenone electrophiles. Further elaboration into the target compounds 8-10 involved dehydration, reduction of the lactam group, and different modes of N-debenzylation. Conformational aspects for lactam compounds 17 and 18 and the modes of ring fusion for the diastereomeric amines 9 and 10 were examined by using proton NMR and infrared spectroscopy.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Chemistry - miscellaneous
× corresponding author
# (joint) last author

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