Synthesis of pyrazolo[1,5-c]quinazoline derivatives through copper-catalyzed tandem reaction of 5-(2-bromoaryl)-1H-pyrazoles with carbonyl compounds and aqueous ammonia

J Org Chem. 2013 Apr 5;78(7):3262-70. doi: 10.1021/jo4001756. Epub 2013 Mar 21.

Abstract

A practical and efficient synthesis of pyrazolo[1,5-c]quinazolines and 5,6-dihydropyrazolo[1,5-c]quinazolines, including several spiro compounds, through copper-catalyzed tandem reaction of 5-(2-bromoaryl)-1H-pyrazoles with carbonyl compounds and aqueous ammonia under air has been developed. Compared with literature methods toward pyrazolo[1,5-c]quinazoline derivatives, the synthetic method reported in this paper has the advantages of readily available and inexpensive starting materials and reagents, broad scope of substrates, and mild reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonia / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Water / chemistry

Substances

  • Ketones
  • Pyrazoles
  • Quinazolines
  • pyrazolo(1,5-c)quinazoline
  • Water
  • Ammonia
  • Copper