-Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2-amino Amides via Deoxygenative C(sp)-H Functionalization.

A logic-based replacement of the carboxylic acid component of the Ugi reaction by quinoline -oxides has been developed. In this approach, the carboxylic isostere, quinoline -oxide, plays a vital role by shifting the equilibria toward the product side with irreversible addition onto the C2-position of the -oxide. Thus, aldehydes react with amines, isocyanides, and quinoline -oxides to furnish quinoline four-component Ugi adducts. The unique reactivity of -oxides with Ugi components opens an efficient synthetic route for the preparation of biologically active compounds.