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N-arylation of 3-alkoxypyrazoles, the case of the pyridines

Abstract : n the course of a research program focused on the preparation of libraries of new chemical entities derived from 3-alkoxypyrazoles, we studied their N-pyridylation using 2, 3 or 4-bromopyridines. This was achieved using Cristau and Taillefer copper-catalyzed arylation method and mostly led to the 3-alkoxy-1H-pyrazol-1-yl pyridine isomer along with lesser amount of the alternative 5-alkoxy-1H-pyrazol-1-yl pyridine. The structures of these isomers were often established via their chemical transformations and sometimes recourse to unambiguous synthetic routes for comparison purposes. The alternative use of 2-fluoropyridine-based arylation was also investigated and lifted some of the limitations encountered in the course of this study.
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Submitted on : Monday, March 15, 2010 - 12:59:13 PM
Last modification on : Tuesday, July 21, 2020 - 3:58:31 AM

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Sandrine Guillou, Frédéric Bonhomme, Di Betina Chahine, Olivier Nesme, Yves Janin. N-arylation of 3-alkoxypyrazoles, the case of the pyridines. Tetrahedron, Elsevier, 2010, 66 (14), pp.2654-2663. ⟨10.1016/j.tet.2010.02.032⟩. ⟨pasteur-00463851⟩

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