Elemental sulfur mediated 2-substituted benzothiazole formation from 2-aminobenzenethiols and arylacetylenes or styrenes under metal-free conditions

被引：30

作者：

Li, Guozheng ^{[1
]}

Jiang, Jingjing ^{[1
]}

Zhang, Feng ^{[1
,2
]}

Xiao, Fuhong ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Key Lab Green Organ Synth & Applicat Hunan Prov, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China

[2] Hunan Agr Univ, Coll Sci, Changsha 410128, Hunan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 47期

基金：

中国国家自然科学基金;

关键词：

S BOND FORMATION; REDOX CONDENSATION REACTION; CATALYZED DIRECT ARYLATION; TRISULFUR RADICAL-ANION; SOLVENT-FREE CONDITIONS; C-S; CARBOXYLIC-ACIDS; SUBSTITUTED BENZOTHIAZOLES; O-CHLORONITROBENZENES; MICROWAVE IRRADIATION;

D O I：

10.1039/c7ob02430d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An oxidative cyclization of 2-aminothiophenols and arylacetylenes or styrenes for the synthesis of 2-alkyl-benzothiazoles and 2-acylbenzothiazoles has been developed. Elemental sulfur was used as the effective oxidant to give the corresponding product in good yield under metal-free conditions.

引用

页码：10024 / 10028

页数：5

共 81 条

[71] A Three-Component Approach to 3,5-Diaryl-1,2,4-thiadiazoles under Transition-Metal-Free Conditions [J].

Xie, Hao ;

Cai, Jinhui ;

Wang, Zilong ;

Huang, Huawen ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2016, 18 (09) :2196-2199

[72] Metal-free oxidative cyclization of 2-aminobenzothiazoles and cyclic ketones enabled by the combination of elemental sulfur and oxygen [J].

Xie, Yanjun ;

Chen, Xiangui ;

Wang, Zhen ;

Huang, Huawen ;

Yi, Bing ;

Deng, Guo-Jun .

GREEN CHEMISTRY, 2017, 19 (18) :4294-4298

[73] Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions [J].

Xie, Yanjun ;

Wu, Jun ;

Che, Xingzong ;

Chen, Ya ;

Huang, Huawen ;

Deng, Guo-Jun .

GREEN CHEMISTRY, 2016, 18 (03) :667-671

[74] Efficient 4,5-dihydro-1H-imidazol-5-one formation from amidines and ketones under transition-metal free conditions [J].

Xie, Yanjun ;

Cheng, Xiufang ;

Liu, Saiwen ;

Chen, Hui ;

Zhou, Wang ;

Yang, Luo ;

Deng, Guo-Jun .

GREEN CHEMISTRY, 2015, 17 (01) :209-213

[75] Visible-light-promoted synthesis of benzothiazoles from 2-aminothiophenols and aldehydes [J].

Ye, Lin-miao ;

Chen, Jie ;

Mao, Peng ;

Mao, Zhi-feng ;

Zhang, Xue-jing ;

Yan, Ming .

TETRAHEDRON LETTERS, 2017, 58 (09) :874-876

[76] Copper-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles, benzoxazoles and benzothiazoles from aromatic alcohols under solvent-free conditions in open air at room temperature [J].

Yu, Jiatao ;

Xu, Jian ;

Lu, Ming .

APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (10) :606-610

[77] External Oxidant-Free Oxidative Cross-Coupling: A Photoredox Cobalt-Catalyzed Aromatic C-H Thiolation for Constructing C-S Bonds [J].

Zhang, Guoting ;

Liu, Chao ;

Yi, Hong ;

Meng, Qingyuan ;

Bian, Changliang ;

Chen, Hong ;

Jian, Jing-Xin ;

Wu, Li-Zhu ;

Lei, Aiwen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) :9273-9280

[78] Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu [J].

Zhang, Guoting ;

Yi, Hong ;

Chen, Hong ;

Bian, Changliang ;

Liu, Chao ;

Lei, Aiwen .

ORGANIC LETTERS, 2014, 16 (23) :6156-6159

[79] Metal Azolate Frameworks: From Crystal Engineering to Functional Materials [J].

Zhang, Jie-Peng ;

Zhang, Yue-Biao ;

Lin, Jian-Bin ;

Chen, Xiao-Ming .

CHEMICAL REVIEWS, 2012, 112 (02) :1001-1033

[80] Multicomponent reactions (MCRs) of arylmethyl bromides, arylamidines and elemental sulfur toward unsymmetric 3,5-diaryl 1,2,4-thiadiazoles [J].

Zhou, Zhen ;

Liu, Miaochang ;

Sun, Song ;

Yao, En ;

Liu, Suqin ;

Wu, Zhiwen ;

Yu, Jin-Tao ;

Jiang, Yan ;

Cheng, Jiang .

TETRAHEDRON LETTERS, 2017, 58 (26) :2571-2573

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