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

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

• multicomponent reactions
• dihydroarenes
• acridines
• terphenyls