Issue 6, 2015

Isoxazole to oxazole: a mild and unexpected transformation

Abstract

3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.

Graphical abstract: Isoxazole to oxazole: a mild and unexpected transformation

Supplementary files

Article information

Article type
Communication
Submitted
09 Oct 2014
Accepted
26 Nov 2014
First published
26 Nov 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2015,51, 1112-1115

Author version available

Isoxazole to oxazole: a mild and unexpected transformation

R. C. F. Jones, A. Chatterley, R. Marty, W. M. Owton and M. R. J. Elsegood, Chem. Commun., 2015, 51, 1112 DOI: 10.1039/C4CC07999J

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