Unique microwave-assisted oxidations of carbamates and analogs utilizing an air stable dichloro-iodobenzene reagent

ORGN 71

Walter Salamant, Department of Chemistry, University of California, Irvine, 516 Rowland Hall CA, Irvine, CA 92697-2025 and Christopher Hulme, #Medicinal Chemistry Technologies, Chemistry Research & Development, Amgen, One Amgen Center Drive, Thousand Oaks, CA 91320.

This poster details the development of an air stable dichloro-iodobenzene species, which affects a complex, one-pot oxidation of carbamates (a,b,b oxidized) generating N-acyliminium ion precursors, suitable for further elaboration. The scope of this unique chemistry was studied and reaction conditions optimized which resulted in a three-component oxidation, facilitated by heat or microwave exposure (5 mins), occurring in high yield (typically >75%). The methodology represents a safe, non-electrochemical, direct chemical oxidation of carbamates and analogs giving N-acyliminium ion precursors. A mechanistic rationale will also be presented.

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics 8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004