Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 12, Pages 4585-4590Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050414g
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[GRAPHICS] Chloroazaphilone is a common structure found in a number of natural products. Reported herein is a practical synthesis of a model chloroazaphilone that utilizes Pb(OAc)(4) oxidation of HClO4/HOAc pyrinium salt in a key one-pot operation. Reaction of this chloroazaphilone with various primary amines to afford the corresponding vinylogous gamma-pyridones was also fully investigated. The isolation of stable enamine intermediates provided direct evidence of reaction mechanisms.
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