Letters in Organic Chemistry

Author(s): Cindy C. Browder, Christopher B. Moss, Matthew B. Kraft, Paige L. Petrucka, Tara S. Morey, Christopher W. Leach and Nicholas C. Gearhart

DOI: 10.2174/157017811795371476

Copper Induced Cyclization of α,β-Unsaturated Carbonyl Compounds to Isoxazoles

Page: [229 - 233] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.

Keywords: Isoxazole, cyclization, copper-mediated, antiinflammatory, pharmaceuticals, antibiotic, ketoxime, anhydrous, Beckmann rearrangement, olefin-tethered substrate