Communication

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

  1. Sandrine Grosse1,
  2. Dr. Christelle Pillard2,
  3. Dr. Stéphane Massip3,
  4. Prof. Jean Michel Léger3,
  5. Prof. Christian Jarry3,
  6. Dr. Stéphane Bourg1,4,
  7. Dr. Philippe Bernard2,
  8. Prof. Gérald Guillaumet1,*

Article first published online: 19 OCT 2012

DOI: 10.1002/chem.201202593

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 47, pages 14943–14947, November 19, 2012

Additional Information

How to Cite

Grosse, S., Pillard, C., Massip, S., Léger, J. M., Jarry, C., Bourg, S., Bernard, P. and Guillaumet, G. (2012), Efficient Synthesis and First Regioselective C-3 Direct Arylation of Imidazo[1,2-b]pyrazoles. Chem. Eur. J., 18: 14943–14947. doi: 10.1002/chem.201202593

Author Information

  1. 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. 2

    Greenpharma S.A.S, 3, allée du Titane, 45100 Orléans (France)

  3. 3

    Université Bordeaux, CNRS FRE 3396, Pharmacochimie, 146 Rue Léo Saignat, 33000 Bordeaux (France)

  4. 4

    Centre de Biophysique Moléculaire UPR-CNRS 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)

*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

Publication History

  1. Issue published online: 13 NOV 2012
  2. Article first published online: 19 OCT 2012
  3. Manuscript Revised: 7 SEP 2012
  4. Manuscript Received: 23 JUL 2012

Funded by

  • Greenpharma Society
  • Conseil Général du Loiret

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Keywords:

  • arylation;
  • C[BOND]C coupling;
  • fused-ring systems;
  • microwave chemistry;
  • palladium;
  • regioselectivity
Thumbnail image of graphical abstract

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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