Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles

被引：36
|
作者：
Luo, Mupeng [1 ,2 ,3 ]
Yuan, Rongju [1 ,2 ,3 ]
Liu, Xuesong [1 ]
Yu, Linqian [1 ]
Wei, Wanguo [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Shanghai Adv Res Inst, 99 Haike Rd, Shanghai 201210, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] ShanghaiTech Univ, Sch Life Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 28期
基金：
中国国家自然科学基金;
关键词：
cyclization; epoxide; iron; oxindole; spiro compounds; ENANTIOSELECTIVE TOTAL-SYNTHESIS; GROWTH-HORMONE SECRETAGOGUES; GARDNERIA-MULTIFLORA MAKINO; RING-OPENING REACTIONS; LEWIS-ACID; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; RADICAL ARYLATION; 3+2 CYCLOADDITION; INDOLE ALKALOIDS;
D O I：
10.1002/chem.201601185
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and highly regioselective iron(III)-catalyzed Friedel-Crafts-type arylation of spiro-epoxyoxindoles with phenols was developed for rapid access to 3-(3-indolyl)-oxindole-3-methanols, which could be further elaborated into benzofuranyl-spirooxindoles under Mitsunobu conditions. When spiro-epoxyoxindoles were reacted with naphthols in the presence of a catalytic amount of FeCl3 center dot 6H(2)O in dichloromethane, they underwent a tandem Friedel-Crafts-type arylation and O-cyclization to yield novel naphthofuranyl-spirooxindoles in excellent yields. This method is applied to enable the efficient and highly regioselective synthesis of a small-molecule inhibitor of the sodium channel Na(v)1.7 (+/-)-XEN402, which is currently in a phase IIb clinical trial for the treatment of pain.
引用
收藏
页码：9797 / 9803
页数：7
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