Synthesis of Isoxazoles via Electrophilic Cyclization

Jesse P. Waldo and Richard C. Larock*

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

J. P. Waldo, R. C. Larock, Org. Lett., 2005, 7, 5203-5205.

DOI: 10.1021/ol052027z

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Abstract

The reaction of various 2-alkyn-1-one O-methyl oximes with ICl, I₂, Br₂, or PhSeBr provided 3,5-disubstituted 4-halo(seleno)isoxazoles in good to excellent yields under mild reaction conditions.

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The Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization: An Efficient Synthesis of Valdecoxib

J. P. Waldo, R. C. Larock, J. Org. Chem., 2007, 72, 9643-9647.

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Key Words

Isoxazoles, Oximes, Ynones

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ID: J54-Y2005-1900