A free-radical cascade methylation/cyclization of N-arylacrylamides and isocyanides with dicumyl peroxide

Org Lett. 2014 Nov 7;16(21):5670-3. doi: 10.1021/ol502738a. Epub 2014 Oct 15.

Abstract

A free-radical cascade methylation/cyclization of a wide range of N-arylacrylamides and isocyanides is demonstrated by using dicumyl peroxide as the methylating reagent, which provides a convenient and selective access to various methylated N-heterocycles such as oxindoles and phenanthridines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemistry*
  • Benzyl Compounds / chemistry*
  • Catalysis
  • Cyanides / chemistry*
  • Cyclization
  • Free Radicals / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Indicators and Reagents / chemistry
  • Indoles / chemistry*
  • Methylation
  • Molecular Structure
  • Phenanthridines / chemistry*

Substances

  • Acrylamides
  • Benzyl Compounds
  • Cyanides
  • Free Radicals
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Indoles
  • Phenanthridines
  • dicumyl peroxide