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Synthesis of Benzisoxazoles by the [3 + 2] Cycloaddition of in situ Generated Nitrile Oxides and Arynes

Anton V. Dubrovskiy and Richard C. Larock*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, Email:

A. V. Dubrovskiy, R. C. Larock, Org. Lett., 2010, 12, 1180-1183.

DOI: 10.1021/ol902921s

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Various substituted benzisoxazoles have been prepared by a [3 + 2] cycloaddition of nitrile oxides and arynes. Both highly reactive intermediates, have been generated in situ by fluoride anion from readily prepared aryne precursors and chlorooximes. The reaction scope is quite general, affording a novel, direct route to functionalized benzisoxazoles under mild reaction conditions.

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Synthesis of Benzisoxazolines by the Coupling of Arynes with Nitrones

C. Lu, A. V. Dubrovskiy, R. C. Larock, J. Org. Chem., 2012, 77, 2279-2284.

Benzyne Click Chemistry: Synthesis of Benzotriazoles from Benzynes and Azides

F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett., 2008, 10, 2409-2412.

Key Words

Benzisoxazoles, Huisgen 1,3-dipolar Cycloaddition

ID: J54-Y2010-0690