Direct synthesis of 3-acylbenzothiophenes via the radical cyclization of 2-alkynylthioanisoles with -oxocarboxylic acids

被引：39

作者：

Liu, Wei ^{[1
]}

Hu, Yao-Qian ^{[1
]}

Hong, Xiao-Yi ^{[1
]}

Li, Guo-Xing ^{[1
]}

Huang, Xiao-Bo ^{[1
]}

Gao, Wen-Xia ^{[1
]}

Liu, Miao-Chang ^{[1
]}

Xia, Yuanzhi ^{[1
]}

Zhou, Yun-Bing ^{[1
]}

Wu, Hua-Yue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 100期

基金：

中国国家自然科学基金;

关键词：

RECEPTOR ANTAGONISTS; ALKYNES; POTENT; DERIVATIVES; DISCOVERY; ACYLATION;

D O I：

10.1039/c8cc07735e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A radical cascade cyclization of 2-alkynylthioanisoles with -oxocarboxylic acids with AgNO3 has been described. This reaction provides a novel route to directly access 3-acylbenzothiophenes from simple chemical feedstocks. In particular, the utility of the approach was demonstrated by its application to the synthesis of a polymerization inhibitor and a raloxifene precursor.

引用

页码：14148 / 14151

页数：4

共 34 条

[1] Diversity-Oriented Synthesis of Substituted Benzo[b]thiophenes and Their Hetero-Fused Analogues through Palladium-Catalyzed Oxidative C-H Functionalization/Intramolecular Arylthiolation [J].

Acharya, Anand ;

Kumar, S. Vijay ;

Ila, Hiriyakkanavar .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) :17116-17125

[2]

Alabugin I., 2017, 254 ACT NAT M EXP WA

[3] Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis [J].

Bergonzini, Giulia ;

Cassani, Carlo ;

Wallentin, Carl-Johan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14066-14069

[4] Interactive SAR studies:: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists [J].

Bettinetti, L ;

Schlotter, K ;

Hübner, H ;

Gmeiner, P .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4594-4597

[5] tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles [J].

Chen, Fei ;

Meng, Qiang ;

Han, Shang-Qing ;

Han, Bing .

ORGANIC LETTERS, 2016, 18 (14) :3330-3333

[6] NOVEL BENZOTHIOPHENECARBOXAMIDOTETRAZOLE, BENZOFURANCARBOXAMIDOTETRAZOLE, AND NAPHTHALENECARBOXAMIDOTETRAZOLE AS POTENTIAL ANTIALLERGY AGENTS [J].

CONNOR, DT ;

CETENKO, WA ;

MULLICAN, MD ;

SORENSON, RJ ;

UNANGST, PC ;

WEIKERT, RJ ;

ADOLPHSON, RL ;

KENNEDY, JA ;

THUESON, DO ;

WRIGHT, CD ;

CONROY, MC .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (05) :958-965

[7]

Disha J., 2010, BIOORG MED CHEM LETT, V20, P5258

[8] 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

[9] Sulfonyl radical-enabled 6-endo-trig cyclization for regiospecific synthesis of unsymmetrical diaryl sulfones [J].

Fu, Rong ;

Hao, Wen-Juan ;

Wu, Ya-Nan ;

Wang, Nan-Nan ;

Tu, Shu-Jiang ;

Li, Guigen ;

Jiang, Bo .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11) :1452-1456

[10] Synthesis of carbonylated heteroaromatic compounds via visible-light-driven intramolecular decarboxylative cyclization of o-alkynylated carboxylic acids [J].

Gao, Fei ;

Wang, Jiu-Tao ;

Liu, Lin-Lin ;

Ma, Na ;

Yang, Chao ;

Gao, Yuan ;

Xia, Wujiong .

CHEMICAL COMMUNICATIONS, 2017, 53 (61) :8533-8536

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