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Reactions of an imidazo[4,5-c]isoxazole-6-carboxylate with electron deficient acetylenes

✍ Scribed by Abutariq Taher; Alexandra M.Z. Slawin; George W. Weaver

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 307 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01681-0

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✦ Synopsis

The synthesis of the first examples of the imidazo[4,5-c]isoxazole ring system has recently been reported, 2 but little is known about the chemistry of this heterocycle. In this paper we describe our investigation into the behaviour of an imidazo[4,5-c]isoxazole-6-carboxylate ester with acetylenic esters and ketones. A complex reaction sequence is found to occur, involving addition of two molecules of alkyne followed by ring opening and fragmentation, leading to the formation of 2-pyrrol-2-yl imidazoles in moderate yield. The mechanism and scope of the reaction is discussed.

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