Direct Cyclopropanation of Quinolinium Zwitterionic Thiolates via Dearomative Reactions

作者：Qiaomei Jin, Cuihua Jiang, Meng Gao, Dongjian Zhang, Shihe Hu, Jian Zhang · 发表于：The Journal of Organic Chemistry · 年份：2021 · DOI：10.1021/acs.joc.1c02175 · 被引用次数：19 · 研究领域：Sulfur-Based Synthesis Techniques、Cyclopropane Reaction Mechanisms、Catalytic Alkyne Reactions

A one-pot, two-step protocol for the synthesis of libraries of remarkable functionalized sulfone analogues of 9b,10,10a,10b-tetrahydro-1 H -cyclopropa[ c ][1,4]thiazino[4,3- a ]quinolines is described. A class of various functionalized molecular skeletons was obtained by cyclopropanation of quinolinium zwitterionic thiolates. The reaction pathway involves the formation of a [2 + 1] cycloaddition intermediate followed by a [5 + 1] cycloaddition.