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A systematic study of reaction of heterocyclic enamines with electrophilic alkynes: a simple and efficient synthetic route to 2-pyridinone-fused heterocycles

✍ Scribed by Mei-Xiang Wang; Wei-Shi Miaoa; Ying Cheng; Zhi-Tang Huang

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 805 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00937-0

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✦ Synopsis

The reaction of heterocyclic enamioes with ethyl propiolate and diethyl acetylenedics&oxylate has been systematically studied. In contrast to their hetemcyclic ketene aminal analogues, heterocyclic enamines reacted with electrophilic e w'a the Michael addition pathway rather thao the aza-ene reaction mechanism. lo the presence of a strong base such as sodium ethotide and sodium hydride, the resulting Michael addition products andenvent cyclocondensation reaction readily to produce 2pyridinone-fused heterocycles in good to excellent yield.

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