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Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives

Meredeth A. McGowan, Camille Z. McAvoy and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

M. A. McGowan, C. Z. McAvoy, S. L. Buchwald, Org. Lett., 2012, 14, 3800-3803.

DOI: 10.1021/ol301700y (free Supporting Information)


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Abstract

A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates proceeds in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives via Pd-catalyzed N-arylation followed by addition of an aldehyde to the crude reaction mixture is also demonstrated.

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Key Words

amidines


ID: J54-Y2012-2380