Issue 6, 2015
From the journal:

Chemical Communications

Isoxazole to oxazole: a mild and unexpected transformation†

Raymond C. F. Jones,*a   Alexander Chatterley,a   Romain Marty,a   W. Martin Owtonb  and  Mark R. J. Elsegooda  

* Corresponding authors

a Department of Chemistry, Loughborough University, Leics. LE11 3TU, UK
E-mail: r.c.f.jones@lboro.ac.uk
Fax: +44 (0)1509 223926
Tel: +44 (0)1509 222557

b Lilly UK, Erl Wood Manor, Windlesham, Surrey, UK

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

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Article information

DOI
https://doi.org/10.1039/C4CC07999J
Article type
Communication
Submitted
09 10 2014
Accepted
26 11 2014
First published
26 11 2014
This article is Open Access
Creative Commons BY license

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

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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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