A Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives

Nair, Vijay ; Mathew, Smitha C. ; Biju, Akkattu T. ; Suresh, Eringathodi (2007) A Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives Angewandte Chemie International Edition, 46 (12). pp. 2070-2073. ISSN 14337851

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Official URL: http://doi.org/10.1002/anie.200604025

Related URL: http://dx.doi.org/10.1002/anie.200604025

Abstract

Two unexpected transformations: The reaction of the Huisgen zwitterion derived from triphenylphosphane and diisopropyl azodicarboxylate (DIAD) with chalcones affords functionalized pyrazolines. In contrast, the reaction with dienones affords pyrazolopyridazines, presumably by Diels–Alder reaction of the initially formed pyrazoline with excess DIAD (see scheme).

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