Organic Letters 2005-08-18

Chemoselective arylamidine cyclizations: mild formation of 2-arylimidazole-4-carboxylic acids.

Joshua C Yoburn, Subramanian Baskaran

Index: Org. Lett. 7(17) , 3801-3, (2005)

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Abstract

A versatile, one-pot synthesis of 2-arylimidazole-4-carboxylic acids from arylamidines and methyl-2-chloroacetoacetate is described. The transformation is chemoselective, and reaction conditions are mild. Moreover, the flexibility of the strategy offers rapid access to two important classes of biaryl compounds, both 2-arylimidazoles and 2-arylpyrimidines, depending simply upon solvent and base selection. [reaction: see text]