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: larock
iastate.edu
A. V. Dubrovskiy, R. C. Larock, Org. Lett., 2010, 12, 1180-1183.
DOI: 10.1021/ol902921s
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Abstract
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
