Organic Letters 2007-04-12

Domino metathesis of 3,6-dihydro-1,2-oxazine: access to isoxazolo[2,3-a]pyridin-7-ones.

Géraldine Calvet, Nicolas Blanchard, Cyrille Kouklovsky

Index: Org. Lett. 9 , 1485, (2007)

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Abstract

[reaction: see text] Strained bicyclic 3,6-dihydro-1,2-oxazine is a reactive substrate in domino metathesis with an external alkene. This general transformation leads to isoxazolo[2,3-a]pyridin-7-one, a versatile scaffold combining chemical functions that could be selectively oxidized or reduced. The synthetic relevance of these domino metathesis products is demonstrated by a straightforward synthesis of a quinolizinone.