Synthesis of novel isoxazole-N-oxides

ORGN 300

Martin G. Kociolek,, School of Science, Penn State Erie, The Behrend College, 4205 College Drive, Erie, PA 16563-0107
Heterocyclic N-oxides are a diverse and important class of molecules. They are found as structural units in numerous compounds of biological interest as well as being versatile synthetic intermediates. One particular class of these compounds that has not received much attention is the isoxazole-N-oxides. Herein, we would like to report our continuing investigations into the synthesis and properties of these interesting heterocycles. We have developed a novel synthesis of a series of 1,2-benzisoxazole-N-oxides from 2-hydroxyaryl oximes in the presence of iodobenzene diacetate. This methodology has also been applied to the synthesis of isoxazole-N-oxide analogues of molecules with biological significance including flavonoids and chalcones. Currently, we are investigating the extension of this methodology to the cyclization of 1,3-oximinoketones to give 3,5-disubstituted isoxazole-N-oxides. The scope, limitations and applications of these novel cyclizations will be discussed.

Heterocycles and Aromatics
1:00 PM-5:20 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 206, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009