An efficient synthesis of 3-triazolyl-2(1H)-quinolones by CuTC-catalyzed azide–alkyne cycloaddition reaction

Authors

  • Samir Messaoudi,

    Corresponding author
    1. Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, Châtenay-Malabry, France
    • Correspondence to: S. Messaoudi, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, CNRS, BioCIS, UMR 8076, LabEx LERMIT, rue J. B. Clément F-92296 Châtenay-Malabry, France. E-mail: samir.messaoudi@u-psud.fr or: mouad.alami@u-psud.fr

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  • Marie Gabillet,

    1. Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, Châtenay-Malabry, France
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  • Jean-Daniel Brion,

    1. Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, Châtenay-Malabry, France
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  • Mouâd Alami

    Corresponding author
    1. Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, Châtenay-Malabry, France
    • Correspondence to: S. Messaoudi, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université Paris-Sud, CNRS, BioCIS, UMR 8076, LabEx LERMIT, rue J. B. Clément F-92296 Châtenay-Malabry, France. E-mail: samir.messaoudi@u-psud.fr or: mouad.alami@u-psud.fr

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Abstract

A facile and efficient Cu(I)-catalyzed azide–alkyne cycloaddition reaction for the synthesis of a series of 3-triazolyl-2(1H)-quinolones 3 have been developed using 3-azido-quinolin-2(1H)-one as the coupling partner. The optimized reaction conditions involve the use of eco- friendly ethanol as the solvent in the presence of copper(I) thiophene-2-carboxylate as the catalyst, to afford good to excellent yields of 3-triazolyl-2(1H)-quinolone derivatives of biological interest. Copyright © 2013 John Wiley & Sons, Ltd.

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