通过 TMSCl 介导的靛红衍生炔丙醇的亲核环化反应合成 2-取代的 3-氯苯并呋喃。
Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols.
机构信息
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China.
出版信息
Org Biomol Chem. 2018 Aug 22;16(33):6133-6139. doi: 10.1039/c8ob01731j.
PMID:30101259
Abstract
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.
摘要
现报道了 TMSCl 介导的色胺酮衍生的炔丙醇的级联环化反应，用于合成 2-取代的 3-氯苯并呋喃。机理研究表明，该反应经过连续的 Meyer-Schuster 重排/亲核加成/分子内环化。在该反应中，TMSCl 不仅作为促进剂，还作为氯源。
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