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

[21] One-pot Synthesis of Benzo[b]thiophenes and Benzo[b]selenophenes from o-Halo-Substituted Ethynylbenzenes: Convenient Approach to Mono-, Bis-, and Tris-Chalcogenophene-Annulated Benzenes [J].

Kashiki, Tomoya ;

Shinamura, Shoji ;

Kohara, Masahiro ;

Miyazaki, Eigo ;

Takimiya, Kazuo ;

Ikeda, Masaaki ;

Kuwabara, Hirokazu .

ORGANIC LETTERS, 2009, 11 (11) :2473-2475

[22] Biomedical Importance of Indoles [J].

Kaushik, Nagendra Kumar ;

Kaushik, Neha ;

Attri, Pankaj ;

Kumar, Naresh ;

Kim, Chung Hyeok ;

Verma, Akhilesh Kumar ;

Choi, Eun Ha .

MOLECULES, 2013, 18 (06) :6620-6662

[23] Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization [J].

Kesharwani, T ;

Worlikar, SA ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2307-2312

[24] Synthesis of 3-iodobenzo[b]thiophenes via iodocyclization/etherification reaction sequence [J].

Kesharwani, Tanay ;

Craig, Jason ;

Del Rosario, Cathlene ;

Shavnore, Renee ;

Komman, Cory .

TETRAHEDRON LETTERS, 2014, 55 (50) :6812-6816

[25]

Kim S., 2013, TETRAHEDRON LETT, V54, P6812

[26] Catalytic Synthesis of Indoles from Alkynes [J].

Krueger, Karolin ;

Tillack, Annegret ;

Beller, Matthias .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2153-2167

[27]

Kunz T., 2012, ANGEW CHEM, V124, P1994

[28] Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers [J].

Kunz, Thomas ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) :1958-1961

[29] Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes [J].

Larock, RC ;

Yum, EK ;

Refvik, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7652-7662

[30] Copper-Catalyzed Thiolation Annulations of 1,4-Dihalides with Sulfides Leading to 2-Trifluoromethyl Benzothiophenes and Benzothiazoles [J].

Li, Chun-Lin ;

Zhang, Xing-Guo ;

Fang, Ri-Yuan ;

Zhong, Ping ;

Li, Jin-Heng .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (20) :7037-7040

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