Biomass-involved, facile and one-pot synthesis of N-aryl-2(3H)-benzoxazolones from methyl 3-dehydroshikimiate

A facile and one-pot method for the synthesis of N-aryl-2(3H)-benzoxazolones via microwave-assisted consecutive reactions between the biomass-derived methyl 3-dehydroshikimiate (3-MDHS), anilines and bis(trichloromethyl) carbonate (BTC) is reported. The protocol includes the efficient generation of the platform compounds N-arylated 2-aminophenols, followed by the smooth annulation reaction induced by BTC. This sequential process represents a metal-free, sustainable and functional group compatible method for the rapid construction of N-aryl-2(3H)-benzoxazolones.