Construction of Benzoxazinones from Anilines and Their Derivatives
Tengfei Zhao, Xiao-Li Xu, Wei‐Yin Sun, Yi Lu
Abstract
Herein we report a strategy concerning Rh(III)-catalyzed direct ortho -C–H bond carbonylation to construct benzoxazinones from anilines and their derivatives with high atom economy. Interestingly, the corresponding amides were generated in situ from anilines when excess Ac 2 O was added and directed the following C–H bond carbonylation to form benzoxazinones. Extensive functional group tolerance can be achieved when the alkyl amide directing groups were installed. Moreover, this method allows convenient derivatization of some drugs with aryl amine groups to show its potential application.
Topics & Concepts
ChemistryAmideAlkylCarbonylationArylAmine gas treatingDerivatizationFunctional groupCombinatorial chemistryGroup (periodic table)Atom economyPrimary (astronomy)Organic chemistryMedicinal chemistryCatalysisPolymerCarbon monoxidePhysicsHigh-performance liquid chromatographyAstronomyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions