Sequential C–C, C–O, and C–N Bond-Forming Reaction of Methyl (–)-3-Dehydroshikimate, Malononitrile, and Bromoalkanes: Simple Synthesis of 2-(Alkylamino)-3-cyanobenzofurans from a Biomass-Derived Substrate

An interesting and simple method was developed for the synthesis of 2-(alkylamino)-3-cyanobenzofurans by consecutive C–C, C–O, and C–N coupling reaction of methyl (–)-3-dehydroshikimate with malononitrile and a bromoalkane or dibromoalkane under microwave conditions. This process represents a metal-free sustainable strategy for the construction of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived starting material.