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Reaction of 2-substituted-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde oximes with electron-deficient olefins and acetylenes

✍ Scribed by Masashi Shirai; Hidekazu Kuwabara; Satoshi Matsumoto; Hidetoshi Yamamoto; Akikazu Kakehi; Michihiko Noguchi

Book ID: 104205307
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 282 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00591-x

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✦ Synopsis

A facile oxime-nitrone isomerization through the 1,2-hydrogen shift in 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde oximes is discussed. The resultant NH-nitrones are trapped by maleimides to afford intermolecular cycloadducts. The reaction of the oximes with electron-deficient acetylenes undergoes via another path initiated by a nucleophilic attack of the oxime to acetylene moiety.

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