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Issue 8, 2010
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An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

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Abstract

An efficient synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reaction partners mediated by TBAF. Reactions are complete within 30 s, giving the target products in good to excellent yield.

Graphical abstract: An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

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Article information


Submitted
27 Oct 2009
Accepted
16 Dec 2009
First published
11 Jan 2010

Chem. Commun., 2010,46, 1272-1274
Article type
Communication

An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

C. Spiteri, P. Sharma, F. Zhang, S. J. F. Macdonald, S. Keeling and J. E. Moses, Chem. Commun., 2010, 46, 1272
DOI: 10.1039/B922489K

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