Use of mesoporous molecular sieves in the production of fine chemicals: Preparation of dihydroquinolinones of pharmaceutical interest from 2’-aminochalcones

Abstract

Solid catalysts can be an alternative to homogeneous mineral Bronsted and Lewis acids for the synthesis of pharmaceuticals provided that diffusional and adsorption properties of reactants and products could be controlled. Structured micro and especially monolayered zeolites and mesoporous material can be active and selective for performing intramolecular cyclization reaction, and more specifically for intramolecular aza-Michael cyclizations of 2¿-aminochalcones to yield aryl-2,3-dihydro-4(1H)-quinolinones of pharmaceutical interest. However, the catalyst deactivates by strong adsorption of the basic quinolinone product. Product desorption has been controlled by optimizing catalyst pore structure and surface composition, together with a proper selection of solvent and reaction temperature. Process intensification for the synthesis of aryl-2,3-4(1H)-quinolinones of pharmaceutical interest has been achieved by preparing catalysts that allow the one pot synthesis of the dihydroquinolinones starting from 2 -nitrochalcones with excellent yields.