Predicting New Ugi–Smiles Couplings: A Combined Experimental and Theoretical Study |
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| Authors: | Dr. Romain Ramozzi Dr. Nicolas Chéron Dr. Laurent El Kaïm Dr. Laurence Grimaud Dr. Paul Fleurat‐Lessard |
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| Affiliation: | 1. Laboratoire de Chimie, UMR 5182, Ecole Normale Supérieure de Lyon, Université de Lyon, 46 allée d'Italie F‐69364 Lyon Cedex 07 (France);2. Laboratoire de Chimie et Procédés, DCSO, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées ParisTech, 828, Boulevard des Maréchaux, F‐91762 Palaiseau Cedex (France);3. Département de Chimie, UMR 8640, Ecole Normale Supérieure, 24 rue Lhomond, 75231 Paris Cedex 05 (France);4. Present address: Fukui Institute for Fundamental Chemistry, Kyoto University, Takano‐Nishihiraki‐cho 34‐4, Sakyou‐ku, Kyoto 606‐8103 (Japan);5. Present address: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138 (USA) |
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| 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. |
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| Keywords: | density functional calculations multicomponent reactions nitrosophenols prediction Ugi– Smiles coupling |
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