A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of <i>N</i>‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐<i>a</i>]indol‐1‐ones Derivatives
Hui Xie, Mei Zhong, Hua‐Jie Kang, Bing Shu, Shang‐Shi Zhang
Abstract
Abstract A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone and tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope and remarkable functional‐group compatibility. Further late‐stage modification of structurally complex drug molecules and mechanistic studies were also accomplished. magnified image
Topics & Concepts
ChemistryAnnulationIntramolecular forceTricyclicCatalysisStereochemistryCascadeCascade reactionCombinatorial chemistryMoleculeOrganic chemistryChromatographyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms