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

共 72 条

[11] A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents [J].

Flynn, BL ;

Verdier-Pinard, P ;

Hamel, E .

ORGANIC LETTERS, 2001, 3 (05) :651-654

[12] Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light [J].

Gao, Li ;

Chang, Bin ;

Qiu, Wenzhao ;

Wang, Lele ;

Fu, Xianzhi ;

Yuan, Rusheng .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) :1202-1207

[13] A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles [J].

Gao, Yuzhen ;

Lu, Guozhang ;

Zhang, Pengbo ;

Zhang, Liangliang ;

Tang, Guo ;

Zhao, Yufen .

ORGANIC LETTERS, 2016, 18 (06) :1242-1245

[14] Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols [J].

Garkhedkar, Amol Milind ;

Gore, Babasaheb Sopan ;

Hu, Wan-Ping ;

Wang, Jeh-Jeng .

ORGANIC LETTERS, 2020, 22 (09) :3531-3536

[15]

Generali J. A., 2009, HOSP PHARM, V44, P670

[16] Synthesis of 3-(Methylsulfonyl)benzo[b]thiophenes from Methyl(2-alkynylphenyl)sulfanes and Sodium Metabisulfite via a Radical Relay Strategy [J].

Gong, Xinxing ;

Wang, Mengjiao ;

Ye, Shengqing ;

Wu, Jie .

ORGANIC LETTERS, 2019, 21 (04) :1156-1160

[17] Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease [J].

Goyal, Deepti ;

Kaur, Amandeep ;

Goyal, Bhupesh .

CHEMMEDCHEM, 2018, 13 (13) :1275-1299

[18] Visible Light Photocatalytic Synthesis of Benzothiophenes [J].

Hari, Durga Prasad ;

Hering, Thea ;

Koenig, Burkhard .

ORGANIC LETTERS, 2012, 14 (20) :5334-5337

[19] Mushroom-Derived Indole Alkaloids [J].

Homer, Joshua A. ;

Sperry, Jonathan .

JOURNAL OF NATURAL PRODUCTS, 2017, 80 (07) :2178-2187

[20] Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives [J].

Isloor, Arun M. ;

Kalluraya, Balakrishna ;

Pai, K. Sridhar .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :825-830

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