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

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

  • Org Lett. 2007 Apr 12;9(8):1485-8. doi: 10.1021/ol0702066.
Géraldine Calvet 1,  Nicolas Blanchard,  Cyrille Kouklovsky
Affiliations

Affiliation

  • 1 Laboratoire de Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d'ORSAY, ICMMO - UMR 8182 - Bâtiment 410 Université Paris-Sud XI, 15 rue Georges Clémenceau, 91405 Orsay Cedex, France.
PMID: 17352486 DOI: 10.1021/ol0702066
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.

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