A simple and convenient two-step, one-pot process synthesis of hetero-imidazole derivatives directly from nitroaminoaryl compounds is described. The reduction of the nitro group by iron in acetic acid and in situ cyclization with triethyl orthoformate, catalyzed by ytterbium triflate, affords the heteroimidazole in good yield. This process avoids the isolation and purification of potentially unstable diamino heterocycles in the traditional two step methods which results in poor yields and slow reaction times. Compared to other one-pot syntheses, this process avoids tin and palladium, thus tolerates a broader range of functional groups. The scope of the reaction includes nitroanilines, nitroaminopyridines, nitroaminothiophenes and nitroaminopyrazines.

Simple and convenient two-step, one-pot synthesis of hetero-imidazoles from nitroaminoaryls catalyzed by ytterbium triflate

243rd National Meeting (2012)

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