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Reactions of an imidazo[4,5-c]isoxazole-6-carboxylate with dimethyl acetylenedicarboxylate; formation of the first example of a [1,4]diazepino[2,3-c]isoxazole

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

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
73 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the first example of a [1,4]diazepino [2,3-c]isoxazole derivative is reported. Reaction of an imidazo[4,5-c]isoxazole with acetylenic esters has been shown to lead to the formation of 2-pyrrol-2-yl imidazoles. Here we report an alternative reaction pathway in which the fused imidazole ring adds a molecule of acetylenic ester, and undergoes ring expansion to a fused [1,4]diazepine. A mechanism for the reaction is discussed.

πŸ“œ SIMILAR VOLUMES

Reactions of an imidazo[4,5-c]isoxazole-
Reactions of an imidazo[4,5-c]isoxazole-6-carboxylate with electron deficient acetylenes
✍ Abutariq Taher; Alexandra M.Z. Slawin; George W. Weaver πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 307 KB

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 e