Pummerer-like Rearrangement Induced Cascade Reactions: Synthesis of Highly Functionalized Imidazoles

J Org Chem. 2023 Jan 6;88(1):739-744. doi: 10.1021/acs.joc.2c02411. Epub 2022 Dec 16.

Abstract

Imidazoles are among the most important pharmacophores in medicinal chemistry. Herein we report a tandem protocol for the synthesis of highly substituted imidazoles through Pummerer-like rearrangement induced cascade reactions including two carbon-nitrogen bond formations, and concomitant aromatization under mild reaction conditions. This procedure gives imidazole derivatives bearing numerous functional groups and could be used for modifying natural products as well as pharmaceuticals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry, Pharmaceutical
  • Imidazoles* / chemistry
  • Nitroimidazoles*

Substances

  • Imidazoles
  • Nitroimidazoles