Access to quinolinones <i>via</i> DMAP-catalysed cascade reaction of 2-substituted benzoic acids with organic azides
Yuan-Yuan He, Mei-Shan Zhu, Yang Gao, Xiao‐Qiang Hu
Abstract
Herein, we report a DMAP-catalysed Curtius rearrangement and intramolecular cyclisation cascade reaction of 2-substituted aryl carboxylic acids with organic azides for the first time. This protocol features simple operation, broad scope and metal-free conditions, furnishing a broad spectrum of biologically attractive heterocycles. The synthetic virtue of this reaction was demonstrated by gram-scale synthesis and applicability toward drug-like molecules.
Topics & Concepts
Curtius rearrangementChemistryCombinatorial chemistryIntramolecular forceCascade reactionBenzoic acidArylOrganic synthesisReaction conditionsBroad spectrumOrganic chemistryCatalysisAlkylCatalytic C–H Functionalization MethodsClick Chemistry and ApplicationsChemical Synthesis and Analysis