Selective Construction of 2-Substituted Benzothiazoles from o-lodoaniline Derivatives S8 and N-Tosylhydrazones

被引：40

作者：

Huang, Yubing ^{[1
]}

Zhou, Peiqi ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 04期

基金：

中国国家自然科学基金;

关键词：

H BOND FUNCTIONALIZATION; C-S BONDS; ELEMENTAL SULFUR; DIAZO-COMPOUNDS; SUBSTITUTED BENZOTHIAZOLES; THIOAMIDE SYNTHESIS; CATALYZED SYNTHESIS; REDOX CONDENSATION; INSERTION; EFFICIENT;

D O I：

10.1021/acs.joc.7b03118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S-8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom bonds.

引用

页码：2460 / 2466

页数：7

共 57 条

[1] Palladium catalyzed one-pot synthesis of 2-(pyridin-4-yl) quinolines via a multicomponent unprecedented reaction of pyridine-4-carbaldehyde, 2-iodoaniline and triethylamine [J].

Ahmed, Atiur ;

Dhara, Shubhendu ;

Singha, Raju ;

Nuree, Yasin ;

Sarkar, Pompy ;

Ray, Jayanta K. .

RSC ADVANCES, 2014, 4 (95) :53137-53141

[2] Synthesis of 2-Aminoquinazolinones via Carbonylative Coupling of ortho-lodoanilines and Cyanamide [J].

Akerbladh, Linda ;

Odell, Luke R. .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (07) :2966-2973

[3] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .20. DECARBOXYLATION OF ALPHA-IMINO ACIDS - MECHANISM AND APPLICATIONS TO THIOAMIDE SYNTHESIS [J].

ALY, MF ;

GRIGG, R .

TETRAHEDRON, 1988, 44 (23) :7271-7282

[4] Assembly of 2-Arylbenzothiazoles through Three-Component Oxidative Annulation under Transition-Metal-Free Conditions [J].

Che, Xingzong ;

Jiang, Jingjing ;

Xiao, Fuhong ;

Huang, Huawen ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2017, 19 (17) :4576-4579

[5] C-H Functionalization/Asymmetric Michael Addition Cascade Enabled by Relay Catalysis: Metal Carbenoid Used for C-C Bond Formation [J].

Chen, Dian-Feng ;

Zhao, Feng ;

Hu, Yue ;

Gong, Liu-Zhu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) :10763-10767

[6] Rhodium(I)-Catalyzed Highly Enantioselective Insertion of Carbenoid into Si-H: Efficient Access to Functional Chiral Silanes [J].

Chen, Diao ;

Zhu, Dong-Xing ;

Xu, Ming-Hua .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (05) :1498-1501

[7] Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds [J].

Chen, Gui ;

Song, Jinshuai ;

Yu, Yinghua ;

Luo, Xuesong ;

Li, Chunsen ;

Huang, Xueliang .

CHEMICAL SCIENCE, 2016, 7 (03) :1786-1790

[8] Room-Temperature Ligand-Free Pd/C-Catalyzed C-S Bond Formation: Synthesis of 2-Substituted Benzothiazoles [J].

Cheng, Yannan ;

Peng, Qian ;

Fan, Weigang ;

Li, Pixu .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12) :5812-5819

[9]

Dev D., 2016, J ORG CHEM, V5, P663

[10] Transition-Metal-Catalyzed Electrophilic Amination: Application of O-Benzoylhydroxylamines in the Construction of the C-N Bond [J].

Dong, Xu ;

Liu, Qing ;

Dong, Yunhui ;

Liu, Hui .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (11) :2481-2511

← 1 2 3 4 5 6 →