Title: Intramolecular Diels-Alder reactions of N-alkenyl-2(1H)-pyrazinones: generation of a novel type of cis-1,7-naphthyridine
Authors: Rombouts, FJR
De Borggraeve, Wim
Toppet, SM
Compernolle, Frans
Hoornaert, GJ # ×
Issue Date: Jan-2001
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron letters vol:42 issue:42 pages:7397-7399
Abstract: The intramolecular Diels Alder reaction of three 1-(omega -alkenyl)-2(1H)-pyrazinones was investigated. Cycloaddition was shown to proceed for 1-(4-pentenyl)- and 1-(5-hexenyl)-2(1H)- pyrazinone 5a and 5b to give the corresponding tricyclic hydrolysed adducts 7a and 7b, but not for the 1-(3-butenyl) derivative 5c. In contrast to 7b. the more strained 7a under,,vent selective acidic solvolysis of the tertiary lactam group to give methyl cis-8-oxo-6-phenyldecahydro[1,7]naphthyridine-6-carboxylate 8. An NMR analysis of 8 is presented, (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4039
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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