Ambient benzotriazole ring opening through intermolecular radical addition to vinyltriazole

Org Lett. 2015 Mar 6;17(5):1208-11. doi: 10.1021/acs.orglett.5b00156. Epub 2015 Feb 16.

Abstract

Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Molecular Structure
  • Nitriles / chemistry
  • Stereoisomerism
  • Triazoles / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Nitriles
  • Triazoles
  • Vinyl Compounds
  • benzotriazole