A New Reaction Mode of 3-Halooxindoles: Acting as C–C–O Three-Atom Components for (3+3) Cycloaddition to Access Indolenine-Fused 2<i>H</i>-1,4-Oxathiines
Ting-Jia Sun, Xue-Song Peng, Wei Sun, Yanping Zhang, Xiaomin Ma, Jian‐Qiang Zhao, Zhen‐Hua Wang, Yong You, Ming‐Qiang Zhou, Jun‐Qing Yin, Wei‐Cheng Yuan
Abstract
Herein, we report an unprecedented implementation of 3-halooxindoles as C–C–O three-atom components for (3+3) cycloaddition with pyridinium 1,4-zwitterionic thiolates, affording structurally diverse indolenine-fused 2 H -1,4-oxathiines in moderate to high yields. A combined experimental and computational mechanistic study suggests that the reaction proceeds through addition of a S conjugate to the o -azaxylylene intermediate, followed by O-Michael addition and a sequential retro-Michael addition/pyridine extrusion pathway.
Topics & Concepts
ChemistryCycloadditionPyridiniumConjugatePyridineAtom (system on chip)ExtrusionMichael reactionCombinatorial chemistryStereochemistryMedicinal chemistryCatalysisOrganic chemistryComputer scienceMathematicsMaterials scienceMetallurgyMathematical analysisEmbedded systemSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsOrganic Chemistry Cycloaddition Reactions