A new method for C(sp2)–H sulfonylmethylation with glyoxylic acid and sodium sulfinates?

Organic & Biomolecular Chemistry Pub Date: 2022-02-03 DOI: 10.1039/D2OB00029F

Abstract

We herein describe a C4 sulfonylmethylation of pyrazol-5-amines with glyoxylic acid and sodium sulfinates. The reaction only needed water as a solvent, and it featured mild reaction conditions, simple operation, and high regioselectivity. Various C4 sulfonylmethylated pyrazol-5-amines were obtained in good to excellent yields. Moreover, this sulfonylmethylation method was applicable for C(sp2)–H sulfonylmethylation of other substrates such as enamines, indoles, and antipyrines by adding a catalyst and changing the solvent. Biological evaluation revealed that some products had antiproliferative activity against cancer cell lines.

Graphical abstract: A new method for C(sp2)–H sulfonylmethylation with glyoxylic acid and sodium sulfinates
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