Iron(III)-Catalyzed Arylation of Spiro-Epoxyoxindoles with Phenols/Naphthols towards the Synthesis of Spirocyclic Oxindoles
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作者
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刊物名称
Chem.-Eur. J.
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年、卷、文献号
2016, 22,
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关键词
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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.
