A Mild Synthesis of 2-Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C-H Functionalization

被引：41

作者：

Gao, Ming-Yuan ^{[2
]}

Li, Jing-Hang ^{[2
]}

Zhang, Shi-Bo ^{[2
]}

Chen, Li Jun ^{[2
]}

Li, Yue-Sheng ^{[1
]}

Dong, Zhi-Bing ^{[1
,2
]}

机构：

[1] Hubei Univ Sci & Technol, Hubei Key Lab Radiat Chem & Funct Mat, Sch Nucl Technol & Chem & Biol, Xianning 437100, Peoples R China

[2] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 02期

关键词：

METAL-FREE SYNTHESIS; S BOND FORMATION; COUPLING REACTIONS; CASCADE REACTIONS; 2-AMINOBENZOTHIAZOLES; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/acs.joc.9b02543

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C-H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing.

引用

页码：493 / 500

页数：8

共 53 条

[21] Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations [J].

Liu, Chao ;

Yuan, Jiwen ;

Gao, Meng ;

Tang, Shan ;

Li, Wu ;

Shi, Renyi ;

Lei, Aiwen .

CHEMICAL REVIEWS, 2015, 115 (22) :12138-12204

[22] Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water [J].

Liu, Xing ;

Zhang, Shi-Bo ;

Zhu, Hui ;

Dong, Zhi-Bing .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) :11703-11711

[23] An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water [J].

Liu, Xing ;

Liu, Min ;

Xu, Wan ;

Zeng, Meng-Tian ;

Zhu, Hui ;

Chang, Cai-Zhu ;

Dong, Zhi-Bing .

GREEN CHEMISTRY, 2017, 19 (23) :5591-5598

[24] Nickel-Catalyzed C-S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes [J].

Liu, Xing ;

Cao, Qiang ;

Xu, Wan ;

Zeng, Meng-Tian ;

Dong, Zhi-Bing .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (38) :5795-5799

[25] Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging [J].

McCutcheon, David C. ;

Paley, Miranda A. ;

Steinhardt, Rachel C. ;

Prescher, Jennifer A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (18) :7604-7607

[26] Cascade reactions in total synthesis [J].

Nicolaou, K. C. ;

Edmonds, David J. ;

Bulger, Paul G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7134-7186

[27] TOTAL SYNTHESIS OF TAXOL [J].

NICOLAOU, KC ;

YANG, Z ;

LIU, JJ ;

UENO, H ;

NANTERMET, PG ;

GUY, RK ;

CLAIBORNE, CF ;

RENAUD, J ;

COULADOUROS, EA ;

PAULVANNAN, K ;

SORENSEN, EJ .

NATURE, 1994, 367 (6464) :630-634

[28] Benzothiazoles: Search for anticancer agents [J].

Noolvi, Malleshappa N. ;

Patel, Harun M. ;

Kaur, Manpreet .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :447-462

[29] Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: a new oxidant for 2-substituted benzothiazoles and benzoxazoles [J].

Praveen, C. ;

Kumar, K. Hemanth ;

Muralidharan, D. ;

Perumal, P. T. .

TETRAHEDRON, 2008, 64 (10) :2369-2374

[30] C-H Functionalization Logic Enables Synthesis of (+)-Hongoquercin A and Related Compounds [J].

Rosen, Brandon R. ;

Simke, Leah R. ;

Thuy-Boun, Peter S. ;

Dixon, Darryl D. ;

Yu, Jin-Quan ;

Baran, Phil S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) :7317-7320

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