N‑Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2- amino Amides via Deoxygenative C(sp2)−H Functionalization

Abstract

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