Metal-Free C–H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents
Jiang Nan, Pu Chen, Xue Gong, Yan Hu, Qiong Ma, Bo Wang, Yangmin Ma
Abstract
A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.
Topics & Concepts
AnnulationCarbonylationChemistryReagentIsocyanateArylCombinatorial chemistrySolventMetalOrganic chemistryCatalysisPolyurethaneCarbon monoxideAlkylCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesAsymmetric Synthesis and Catalysis