A versatile synthesis of diverse 3,4-fused cinnolines via the base-catalysed condensation of 2-amino-2'-nitrobiaryls

Chem Commun (Camb). 2007 Jun 28:(24):2506-8. doi: 10.1039/b618318b. Epub 2007 Mar 21.

Abstract

Benzo[c]cinnolines, thieno[3,2-c]cinnolines, pyrido[3,2-c]cinnolines and the previously undescribed quinoxalino[6,7-c]cinnoline ring system are conveniently prepared by a short synthetic route comprised of Suzuki coupling, base-catalysed cyclisation and deoxygenation. The use of tandem borylation-Suzuki coupling further extends the scope of this process to include highly substituted benzo[c]cinnolines.

MeSH terms

  • Biphenyl Compounds / chemistry*
  • Boronic Acids / chemistry
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Molecular Structure

Substances

  • Biphenyl Compounds
  • Boronic Acids
  • Heterocyclic Compounds, 2-Ring
  • cinnoline