Palladium-catalyzed synthesis of conformationally constrained small cyclic peptides via intramolecular Buchwald-Hartwig C-N coupling

ORGN 562

Javed Iqbal, javediqbaldrf@hotmail.com, Discovery Research, Dr. Reddy's Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad, 500049, India, V. Balraju, balrajuv@rediffmail.com, Discovery Research, Dr. Reddy's Laboratories Ltd., University of Hyderabad, School of Chemistry, Bollaram Road, Miyapur, Hyderabad, 500 049, A.P, India, and Mariappan Periasamy, mpsc@uohyd.ernet.in, School of Chemistry, University of Hyderabad, Central University P.O, Hyderabad-500 046, India.
Small peptides having a 3-bromobenzyl group at the C-termini and a 3-aminophenyl group at the N-termini undergo an efficient Pd(OAc)2/BINAP catalyzed intramolecular Buchwald-Hartwig amination reactions to afford diarylamine contained cyclic peptides in good yields. An intramolecular cyclization of these diarylamine cyclic peptides in the presence of catalytic palladium acetate (50mol%) gave the correspongding carbazole containing cyclic peptides in good yield.

 

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