Metal-free nitrogenation of 2-acetylbiphenyls: expeditious synthesis of phenanthridines

Org Lett. 2015 May 1;17(9):2206-9. doi: 10.1021/acs.orglett.5b00797. Epub 2015 Apr 15.

Abstract

An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Metals / chemistry
  • Molecular Structure
  • Nitrogen / chemistry*
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry

Substances

  • Azides
  • Metals
  • Phenanthridines
  • Nitrogen