Formal [4 + 1] Annulation of α-Arylhydrazonoketones and Dimethylsulfoxonium Methylide: One-pot Synthesis of Substituted Pyrazoles and Dihydropyrazoles

J Org Chem. 2016 Jul 15;81(14):6036-41. doi: 10.1021/acs.joc.6b01127. Epub 2016 Jun 30.

Abstract

A formal [4 + 1] annulation of readily available α-arylhydrazonoketones and trimethylsulfoxonium iodide in the presence of cesium carbonate is described involving a sequential Corey-Chaykovsky reaction and intramolecular nucleophilic cyclization process. Substituted pyrazoles were obtained exclusively from the reactions of α-arylhydrazono-β-oxo-amides and trimethylsulfoxonium iodide in moderate to good yields, whereas the reactions of α-arylhydrazono-β-oxo-ketone/α-arylhydrazono- β-oxo-ester afforded the corresponding dihydropyrazoles in good yields.

Publication types

  • Research Support, Non-U.S. Gov't