Predicting new Ugi-smiles couplings: a combined experimental and theoretical study

Abstract

Following our previous mechanistic studies of multicomponent Ugi-type reactions, theoretical calculations have been performed to predict the efficiency of new substrates in Ugi-Smiles couplings. First, as predicted, 2,4,6-trichlorophenol experimentally gave the corresponding aryl-imidate. Theoretical predictions of nitrosophenols as good acidic partners were then successfully confirmed by experiments. In the latter case, the reaction offers a new access to benzimidazoles.

Keywords: Ugi-Smiles coupling; density functional calculations; multicomponent reactions; nitrosophenols; prediction.