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: larockiastate.edu
A. V. Dubrovskiy, R. C. Larock, Org. Lett., 2010, 12, 1180-1183.
DOI: 10.1021/ol902921s (free Supporting Information)
see article for more reactions
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.
see article for more examples
C. Lu, A. V. Dubrovskiy, R. C. Larock, J. Org. Chem., 2012, 77, 2279-2284.
F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett., 2008, 10, 2409-2412.