DMSO as a C1 Source for [2 + 2 + 1] Pyrazole Ring Construction via Metal-Free Annulation with Enaminones and Hydrazines

Org Lett. 2022 Jan 14;24(1):228-233. doi: 10.1021/acs.orglett.1c03879. Epub 2021 Dec 15.

Abstract

A cascade reaction between enaminones, hydrazines, and dimethyl sulfoxide (DMSO) for the synthesis of 1,4-disubstituted pyrazoles catalyzed by molecular iodine in the presence of Selectfluor has been realized. DMSO plays a dual role as the C1 source and the reaction medium. In addition, the synthesis of 1,3,4-trisubstituted pyrazoles using aldehydes as alternative C1 building blocks has also been achieved.