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Novel Synthesis of Highly Functionalized Pyrazolines and Pyrazoles by Triphenylphosphine-Mediated Reaction of Dialkyl Azodicarboxylate with Allenic Esters

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posted on 25.05.2006, 00:00 by Vijay Nair, A. T. Biju, Kishor Mohanan, Eringathodi Suresh
Reaction of the Huisgen zwitterion, derived from triphenylphosphine and dialkyl azodicarboxylate, with allenic esters affords highly functionalized pyrazolines and pyrazoles. The crystal structure of pyrazoline derivative 7a showed extensive C−H···O interactions. Pyrazole formation proceeds via a novel nitrogen to carbon migration of the carboalkoxy group.