An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template.
[reaction: see text] We describe herein a new base-mediated process for the formation of N-arylpyridinones 2 and their use for the preparation of naphthyridones and quinolines. The cyclization of various hindered enamines with methyl propiolate proceeds efficiently in the presence of NaOH to afford the corresponding N-arylpyridinones. These substrates were then found to undergo subsequent cyclizations to afford highly functionalized naphthyridones and quinolines.
Savarin
Cécile G
CG
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. cecile_savarin@merck.com
Murry
Jerry A
JA
Dormer
Peter G
PG