Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade

J Am Chem Soc. 2013 Aug 28;135(34):12548-51. doi: 10.1021/ja406131a. Epub 2013 Aug 19.

Abstract

We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.

Publication types

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

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / chemistry
  • Amination
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Organoselenium Compounds / chemistry*
  • Phenazines / chemical synthesis*
  • Phenazines / chemistry
  • Rhodium / chemistry*

Substances

  • Acridines
  • Organoselenium Compounds
  • Phenazines
  • Rhodium