Predicting New Ugi-Smiles Couplings: A Combined Experimental and Theoretical Study

Romain Ramozzi (1, 2, 3, 4) , Nicolas Chéron (1, 3) , Laurent El Kaim (3) , Laurence Grimaud (4) , Paul Fleurat-Lessard (1)

1 LC - Laboratoire de Chimie - UMR5182
2 UCP - Unité de Chimie et Procédés
3 DCSO - Laboratoire de synthèse organique
4 PASTEUR - Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640)

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.

Domains: Chemical Sciences; Organic chemistry

Romain Ramozzi, Nicolas Chéron, Laurent El Kaim, Laurence Grimaud, Paul Fleurat-Lessard. Predicting New Ugi-Smiles Couplings: A Combined Experimental and Theoretical Study. Chemistry - A European Journal, 2014, 20 (29), pp.9094-9099. ⟨10.1002/chem.201400336⟩. ⟨hal-01057795⟩