title: 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.
authors.affiliation: Laboratoire de Chimie, UMR 5182, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie F-69364 Lyon Cedex 07 (France); Laboratoire de Chimie et Procédés, DCSO, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées ParisTech, 828, Boulevard des Maréchaux, F-91762 Palaiseau Cedex (France); Département de Chimie, UMR 8640, Ecole Normale Supérieure, 24 rue Lhomond, 75231 Paris Cedex 05 (France); Present address: Fukui Institute for Fundamental Chemistry, Kyoto University, Takano-Nishihiraki-cho 34-4, Sakyou-ku, Kyoto 606-8103 (Japan).
authors.forename: Romain
authors.initials: R
authors.lastname: Ramozzi
authors.forename: Nicolas
authors.initials: N
authors.lastname: Chéron
authors.forename: Laurent
authors.initials: L
authors.lastname: El Kaïm
authors.forename: Laurence
authors.initials: L
authors.lastname: Grimaud
authors.forename: Paul
authors.initials: P
authors.lastname: Fleurat-Lessard
keywords: Ugi-Smiles coupling; density functional calculations; multicomponent reactions; nitrosophenols; prediction