Regiodivergent Synthesis of 3,4- and 4,5-Disubstituted N-Methylpyrazoles from 4-Acyl-1 H-pyrrole-2,3-dione and Methylhydrazine

J Org Chem. 2022 Jul 1;87(13):8544-8550. doi: 10.1021/acs.joc.2c00657. Epub 2022 Jun 10.

Abstract

A simple, efficient and highly regioselective method for the preparation of 3,4- and 4,5-disubstituted N-methylpyrazoles in a one-pot procedure is reported. The methodology developed was based on the regiochemical control of the reaction of 4-acyl-1H-pyrrole-2,3-diones and methylhydrazine with an influence of the addition or absence of acid and the substrate structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Monomethylhydrazine*
  • Pyrroles* / chemistry

Substances

  • Pyrroles
  • Monomethylhydrazine