An advanced and novel one-pot synthetic method for diverse benzo[c]chromen-6-ones by transition-metal free mild base-promoted domino reactions of substituted 2-hydroxychalcones with β-ketoesters and its application to polysubstituted terphenyls

Abstract

Novel and efficient one-pot syntheses of a variety of benzo[c]chromen-6-one derivatives were accomplished using Cs₂CO₃-promoted reactions between substituted 2-hydroxychalcones and β-ketoesters. These reactions involved domino Michael addition/intramolecular aldol/oxidative aromatization/lactonization and provided a rapid synthetic route for the production of biologically interesting novel benzo[c]chromen-6-one molecules bearing several different substituents on benzene rings. As an application of this methodology, several synthesized benzo[c]chromen-6-ones were transformed into highly functionalized novel terphenyls.