Novel one-step methodologies with trimethylsilylcyanide affording three chemotypes via new microwave mediated pseudo-Strecker and Strecker domino reactions

ORGN 507

C. Hulme, Hulme_Christopher@Lilly.com, T. Masquelin, J. Schwerkoske, H. Bui, M. Denney, and L. Sachs. High-Throughput Medicinal Chemistry and Analytical Technologies, Discovery Chemistry and Research Technologies, Eli Lilly and Company, Indianapolis, IN 46285
One step microwave mediated syntheses of arrays of 3-aminoimidazo[1,2a] pyridines iminoaryl-imidazopyridines and 3-(amino-1-cyano)imidazopyridines are reported via domino Strecker reactions. Reactions are performed in methanol by simply mixing a-amino-pyridines, 1, aldehydes and trimethylsilylcyanide (TMSCN) with distinct reagent stoichiometries, catalyzed by PS-Scandium triflate, to afford one of three potential products in high isolated yield. The chemistry reflects the renaissance of high temperature microwave enabled chemistry and represents examples of novel 3-center-3-component, 3-center-4-component and 3-center-5-component multi-component reactions, giving products 2, 3 and 4 with specific reagent stoichiometries controlling the reaction end-point.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006