Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4‐<i>a</i>]indolone and Dihydropyrimido [1,6‐a]indolone <i>via</i> Rh(III)‐catalyzed [3+3] or [4+2] C−H Annulation
Junyu Chen, Tianshuo Zhong, Xiangyun Zheng, Chuanliu Yin, Lei Zhang, Jian Zhou, Xinpeng Jiang, Chuanming Yu
Abstract
Abstract A formation of fused tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones and dihydropyrimido[1,6‐ a ]indol‐1(2 H )‐ones via Rh(III)‐catalyzed [3+3] or [4+2] annulation of N ‐methoxy‐1 H ‐indole‐1‐carboxamides with sulfoxonium ylides has been developed. These selective annulation reactions were carried out by switching the additives and notable features of this protocol were low catalyst loading and a broad substrate scope providing the corresponding products in up to 99% yields. magnified image
Topics & Concepts
AnnulationChemistryTricyclicCatalysisIndole testSubstrate (aquarium)StereochemistryScope (computer science)Combinatorial chemistryMedicinal chemistryOrganic chemistryProgramming languageGeologyComputer scienceOceanographyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions