Metal-Free Synthesis of 2-Aminobenzothiazoles via I2-Catalyzed Tandem Cyclization Reaction of Amines and Carbon Disulfide

被引：4

作者：

Chen, Ting ^{[1
]}

Feng, Wei ^{[1
]}

Yang, Ruitong ^{[1
]}

Chen, Shanping ^{[1
]}

Deng, Guo-Jun ^{[1
,2
]}

机构：

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

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Hunan, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 08期

基金：

中国国家自然科学基金;

关键词：

Sulfur heterocycles; C-H functionalization; Cyclization; Tandem reaction; Transition-metal-free; Amines; Iodine; N-Heterocycles; RETINOIC ACID METABOLISM; S BOND FORMATION; BIOLOGICAL EVALUATION; C-H; CATALYZED SYNTHESIS; DIRECT AMINATION; AROMATIC-AMINES; COPPER-OXIDE; ONE-POT; INHIBITORS;

D O I：

10.1002/cjoc.202300610

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient approach for the construction of 2-aminobenzothiazoles via I-2-catalyzed tandem cyclization reaction of amines and carbon disulfide has been developed. The present approach starts from simple and readily available starting materials, affording a series of 2-aminobenzothiazoles in up to 89% yields under metal-free conditions. In this work, C-H/N-H functionalization was achieved and multiple C-hetero bonds were successfully constructed in one pot.

引用

页码：846 / 852

页数：7

共 50 条

[31] Synthesis of 2-Aminoquinazolines through I2-Catalyzed Cyclization of 2-Aminoaryl Ketone Oximes and Isocyanides
Lin, Huishu
Huang, Rongxiuyuan
Wang, Xu
Fu, Jinping
Liu, Yuyuan
Yi, Yi
Pan, Yingming
ADVANCED SYNTHESIS & CATALYSIS, 2025,
[32] Merrifield resin supported phenanthroline-Cu(I): a highly efficient and recyclable catalyst for the synthesis of 2-aminobenzothiazoles via the reaction of 2-haloanilines with isothiocyanates
Yang, Jin
Li, Pinhua
Wang, Lei
TETRAHEDRON, 2011, 67 (31) : 5543 - 5549
[33] DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C-H sulfurization: a new route to 2-aminobenzothiazoles
Yao, Guangkai
Wang, Bing-Feng
Yang, Shuai
Zhang, Zhi-Xiang
Xu, Han-Hong
Tang, Ri-Yuan
RSC ADVANCES, 2019, 9 (06) : 3403 - 3406
[34] Synthesis of 2-alkenylfurans via a Ag(i)-catalyzed tandem cyclization/cross-coupling reaction of enynones with iodonium ylides
Peng, Haiyun
Wan, Yinbo
Zhang, Yu
Deng, Guisheng
CHEMICAL COMMUNICATIONS, 2020, 56 (09) : 1417 - 1420
[35] Synthesis of 2,3-unsaturated glycosides via metal-free Ferrier reaction
De, Kavita
Legros, Julien
Crousse, Benoit
Bonnet-Delpon, Daniele
TETRAHEDRON, 2008, 64 (46) : 10497 - 10500
[36] The Synthesis of 2-(Arylthio)arylcyanamides via Copper-Catalyzed Domino Intermolecular C-S Cross-Coupling Reaction of 2-Aminobenzothiazoles with Aryl Iodides
Shao, Yin-Lin
Zhang, Xiao-Hong
Han, Jiang-Sheng
Zhong, Ping
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (09) : 1137 - 1146
[37] An I2-catalyzed oxidative cyclization for the synthesis of indolizines from aromatic/aliphatic olefins and α-picoline derivatives
Xiang, Likui
Zhang, Fuming
Chen, Baohua
Pang, Xiaobo
Yang, Xiaodong
Huang, Guosheng
Yan, Rulong
RSC ADVANCES, 2015, 5 (37) : 29424 - 29427
[38] Synthesis of indolo[2,1-: α] isoquinoline derivatives via metal-free radical cascade cyclization
Hu, Xu-Yang
Xu, Hai-Feng
Chen, Qiang
Pan, You-Lu
Chen, Jian-Zhong
Organic and Biomolecular Chemistry, 2021, 19 (47): : 10376 - 10384
[39] Synthesis of indolo[2,1-α]isoquinoline derivatives via metal-free radical cascade cyclization
Hu, Xu-Yang
Xu, Hai-Feng
Chen, Qiang
Pan, You-Lu
Chen, Jian-Zhong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (47) : 10376 - 10384
[40] Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls
Lu, Yuling
Chen, Li
Chen, Xia
Yao, Meng
Luo, Zengwei
Zhang, Yonghui
SYNTHESIS-STUTTGART, 2020, 52 (02): : 290 - 296

← 1 2 3 4 5 →