AlCl₃·6H₂O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol

Molecules. 2017 May 16;22(5):742. doi: 10.3390/molecules22050742.

Abstract

A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl₃·6H₂O has been developed for a well-known important natural product, celastrol, resulting in a series of derivatives for further biological evaluation. The catalyst loading was reduced to 5 mol %, the reaction proceeds at ambient temperature and reaction time is only 3 h. The product yields range from 20% to 99%. A reaction mechanism is also proposed, based on our experiment results.

Keywords: AlCl3·6H2O; Friedel-Crafts alkylation; celastrol; indole.

MeSH terms

  • Alkylation
  • Catalysis
  • Indoles / chemistry*
  • Molecular Structure
  • Pentacyclic Triterpenes
  • Stereoisomerism
  • Triterpenes / chemistry*

Substances

  • Indoles
  • Pentacyclic Triterpenes
  • Triterpenes
  • celastrol