Synthesis of isoxazoles via electrophilic cyclization

ORGN 47

Jesse P. Waldo, jwaldo@iastate.edu and Richard C. Larock, larock@iastate.edu. Department of Chemistry, Iowa State University, 3701 Gilman Hall, Ames, IA 50011
Abstract

3,4,5-Trisubstituted isoxazoles are prepared by the electrophilic cyclization of various 2-alkyn-1-one O-methyl oximes. This reaction affords good to excellent yields of the desired products under very mild reaction conditions. The reaction tolerates a variety of functional groups, including ester and TIPS groups, and various heterocycles. Halogens and phenylselenium bromide have been used as electrophiles in this reaction.

 

Heterocycles and Aromatics
1:00 PM-5:00 PM, Sunday, 13 March 2005 Convention Center -- Room 11A, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005