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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Application of heterocyclic aldehydes as components in Ugi-Smiles couplings.
Beilstein J Org Chem
September 2016
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
Efficient one-pot Ugi-Smiles couplings are reported for the use of furyl-substituted aldehyde components. In the presence of these heterocyclic aldehydes, reactions tolerated variations in amine components and led to either isolated -arylamide Ugi-Smiles adducts or -arylepoxyisoindolines, products of tandem Ugi-Smiles Diels-Alder cyclizations, in moderate yields. A thienyl-substituted aldehyde was also a competent component for Ugi-Smiles adduct formation.
View Article and Find Full Text PDFPredicting new Ugi-smiles couplings: a combined experimental and theoretical study.
Chemistry
July 2014
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).
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.
View Article and Find Full Text PDFSubstituent effects in Ugi-smiles reactions.
J Phys Chem A
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Ecole Normale Supérieure de Lyon, Laboratoire de Chimie, Université de Lyon, UMR 5182, 46 allée d'Italie, F-69364 Lyon Cedex 07, France.
In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system (J. Org. Chem.
View Article and Find Full Text PDFUgi-Smiles couplings of 4-substituted pyridine derivatives: a fast access to chloroquine analogues.
Org Lett
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DCSO-UMR 7652: CNRS-ENSTA-Ecole Polytechnique, Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75739 Paris Cedex 15, France.
4-Hydroxy and mercapto pyridines were successfully tested in Ugi-Smiles couplings. Such multicomponent reactions applied to quinoline derivatives afford a very convenient and short synthesis of antimalarial analogues.
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