Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines

被引：11

作者：

Cai, Tao ^{[1
]}

Feng, Chengjie ^{[1
]}

Shen, Fangqi ^{[1
]}

Bian, Kejun ^{[1
]}

Wu, Chunlei ^{[1
]}

Shen, Runpu ^{[1
]}

Gao, Yuzhen ^{[2
]}

机构：

[1] Shaoxing Univ, Dept Coll Chem & Chem Engn, Shaoxing 312000, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 04期

关键词：

Benzothiophenes; Cyclization; Indoles; Heterocycles; Homogeneous catalysis; Synthetic methods; TRANSITION-METAL-FREE; ELECTROPHILIC CYCLIZATION; RADICAL CYCLIZATION; EFFICIENT SYNTHESIS; CASCADE ANNULATION; ONE-POT; BENZOTHIOPHENES; ALKYNES; 2-ALKYNYLTHIOANISOLES; DISULFIDES;

D O I：

10.1002/ejoc.202001465

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.

引用

页码：653 / 656

页数：4

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