Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols.
Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols.
复制标题
DOI：
10.1039/c8ob01731j
复制
发表时间：
2018-08
影响因子：
3.2
通讯作者：
Zhou Sun;K. Xiang;Hua Tao;Li-Cheng Guo;Ying Li
中科院分区：
文献类型：
--
作者：
Zhou Sun;K. Xiang;Hua Tao;Li-Cheng Guo;Ying Li
本文报道了一种由三甲基氯硅烷介导的靛红炔丙醇级联成环反应合成2-取代3-氯苯并呋喃的方法。机理研究表明，这是通过一个连续的Meyer-Schuster重排/亲核加成/分子内成环。TMSC 1在该方案中不仅充当促进剂，而且充当氯源。
A TMSCl-mediated cascade annulation of isatin-derived propargylic alcohols for the synthesis of 2-substituted 3-chlorobenzofurans is now reported. Mechanistic investigations showed that this proceeded through a sequential Meyer-Schuster rearrangement/nucleophilic addition/intramolecular annulation. TMSCl not only acts as a promoter, but also acts as a chlorine source in this protocol.