Facile synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines via Ugi four-component reaction followed by Cu-catalyzed aryl-amide, C–N bond coupling

Abstract

A simple one-pot two-step reaction comprising an Ugi four-component reaction (Ugi-4CR) and copper-catalyzed intramolecular amide-aryl cyclization of heteroaryl chloride with amide has been developed for the synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines in moderate to good yields. The synthesized pyrrolo-fused quinoline was further examined for Pd-catalyzed intramolecular cyclization to afford [1,4]oxazine-fused pyrrolo quinoline 11 and to nucleophilic substitution reactions with allyl bromide and methyl iodide to afford the corresponding allyl and methyl ethers, 12 and 13, respectively.