Gold(<scp>iii</scp>)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks
Jingjing Huang, Han Su, Ming Bao, Lihua Qiu, Yuanqing Zhang, Xinfang Xu
Abstract
A gold-catalyzed 6-endo-dig azide-yne cyclization/O-H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs.
Topics & Concepts
Alkoxy groupCascadeCatalysisCascade reactionAzideChemistryCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryAlkylChromatographyCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods