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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)
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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https://hal-polytechnique.archives-ouvertes.fr/hal-01057795
Contributor : Denis Roura <>
Submitted on : Monday, August 25, 2014 - 2:12:10 PM
Last modification on : Tuesday, September 22, 2020 - 3:59:10 AM

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ENS-LYON | CNRS | X | X-DCSO | ENSTA_UCP | ENSTA | PARISTECH | UPMC | HAL-CHIMIE-ENSLYON | PASTEUR_UMR8640 | ENS-PARIS | INC-CNRS | UNIV-LYON1 | X-DEP-CHIM | SORBONNE-UNIVERSITE | SU-SCIENCES | UDL | PSL

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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, Wiley-VCH Verlag, 2014, 20 (29), pp.9094-9099. ⟨10.1002/chem.201400336⟩. ⟨hal-01057795⟩

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