Sustainable Access to Acridin-9-(10 H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction

Molecules. 2020 Nov 27;25(23):5565. doi: 10.3390/molecules25235565.

Abstract

A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m-terphenyl moieties. Overall, the route generates three C-C and one C-N bond and has the advantage of requiring a single chromatographic separation.

Keywords: acridines; dihydroarenes; multicomponent reactions; terphenyls.

MeSH terms

  • Acridines / chemistry*
  • Aniline Compounds / chemistry
  • Catalysis
  • Chalcones / chemistry
  • Cyclization
  • Esters / chemistry
  • Intercalating Agents / chemistry*
  • Molecular Structure
  • Terphenyl Compounds / chemistry*

Substances

  • Acridines
  • Aniline Compounds
  • Chalcones
  • Esters
  • Intercalating Agents
  • Terphenyl Compounds