Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines

Org Lett. 2019 May 3;21(9):3337-3341. doi: 10.1021/acs.orglett.9b01082. Epub 2019 Apr 19.

Abstract

The in situ formed ruthenium catalytic system ([Ru]/L) was found to be highly selective for the dehydrogenative coupling reaction of 2-aminophenyl ketones with amines to form quinazoline products. The deaminative coupling reaction of 2-aminobenzamides with amines led to the efficient formation of quinazolinone products. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Benzamides / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Cycloaddition Reaction
  • Ketones / chemistry*
  • Ligands
  • Quinazolines / chemical synthesis*
  • Quinazolinones / chemical synthesis
  • Ruthenium / chemistry*

Substances

  • Amines
  • Benzamides
  • Coordination Complexes
  • Ketones
  • Ligands
  • Quinazolines
  • Quinazolinones
  • Ruthenium