Copper-catalyzed, multicomponent coupling of alkynes, pyridine, and acid chlorides: A mild, one-pot route to alpha-alkynated heterocycles

ORGN 407

Ramsay E. Beveridge, ramsay.beveridge@mail.mcgill.ca1, Bruce A. Arndtsen, bruce.arndtsen@mcgill.ca2, and Daniel A. Black2. (1) Dept. of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC H3A 2K6, Canada, (2) Department of Chemistry, McGill University, 801 Sherbrooke St. W, Montreal, QC H3A 2K6, Canada
Polysubstituted heterocycles represent an important class of compounds of broad biological and synthetic utility. Methods for the incorporation of substitutents directly onto heterocycles typically require harsh conditions and/or multi-step synthetic schemes. This poster will describe our design of a new copper (I) catalyzed, multicomponent reaction of various aromatic N-heterocycles (pyridines, quinolines, and imidazoles) with activating agents (chloroformates or acid chlorides) and terminal alkynes in one pot to generate alpha-alkynylated heterocycles. The products of this reaction are the result of the fast, room temperature addition of the copper(I) acetylide to the N-acylazinium salt formed in situ representing a mild and efficient method of alkynylating azines. The overall mechanism of this reaction and its synthetic scope will be provided.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005