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Efficient Synthesis and First Regioselective C-3 Direct Arylation of Imidazo[1,2-b]pyrazoles

Authors

  • Sandrine Grosse,

    1. Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2 (France), Fax: (+33) 38 41 72 81
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  • Dr. Christelle Pillard,

    1. Greenpharma S.A.S, 3, allée du Titane, 45100 Orléans (France)
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  • Dr. Stéphane Massip,

    1. Université Bordeaux, CNRS FRE 3396, Pharmacochimie, 146 Rue Léo Saignat, 33000 Bordeaux (France)
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  • Prof. Jean Michel Léger,

    1. Université Bordeaux, CNRS FRE 3396, Pharmacochimie, 146 Rue Léo Saignat, 33000 Bordeaux (France)
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  • Prof. Christian Jarry,

    1. Université Bordeaux, CNRS FRE 3396, Pharmacochimie, 146 Rue Léo Saignat, 33000 Bordeaux (France)
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  • Dr. Stéphane Bourg,

    1. Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2 (France), Fax: (+33) 38 41 72 81
    2. Centre de Biophysique Moléculaire UPR-CNRS 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
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  • Dr. Philippe Bernard,

    1. Greenpharma S.A.S, 3, allée du Titane, 45100 Orléans (France)
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  • Prof. Gérald Guillaumet

    Corresponding author
    1. Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2 (France), Fax: (+33) 38 41 72 81
    • Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR-CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans cedex 2 (France), Fax: (+33) 38 41 72 81
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Abstract

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Highly regioselective: An efficient synthesis of the imidazo[1,2-b]pyrazole core has been developed, and the first regioselective palladium-catalyzed direct arylation of the C-3 position is described (see scheme). Good to excellent yields were obtained for a wide range of aryl partners with electron-rich and electron-poor substituents. This methodology allows rapid access to a large variety of imidazo[1,2-b]pyrazole products and could open the way to the design of new biologically active compounds.

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