Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol

Org Biomol Chem. 2015 Jun 21;13(23):6580-6. doi: 10.1039/c5ob00755k. Epub 2015 May 18.

Abstract

A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid, AlCl3, is required to promote the cyclization for less electron-rich anilines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / chemistry
  • Benzaldehydes / chemistry
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Palladium / chemistry*
  • Phosphines / chemistry

Substances

  • 2-bromobenzaldehyde
  • Acridines
  • Benzaldehydes
  • Phosphines
  • Palladium