Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst

被引:106
作者
He, Wei-Bao [1 ]
Gao, Lan-Qing [1 ]
Chen, Xin-Jie [3 ]
Wu, Zhi-Lin [4 ]
Huang, Ying [2 ]
Cao, Zhong [2 ]
Xu, Xin-Hua [1 ]
He, Wei-Min [2 ]
机构
[1] Hunan Univ, Dept Chem, Changsha 410082, Hunan, Peoples R China
[2] Changsha Univ Sci & Technol, Hunan Prov Key Lab Mat Protect Elect Power & Tran, Changsha 410114, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China
[4] Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China
关键词
Air; Photocatalysis; Cascade reaction; Photocatalyst-free; 2-Aminobenzothiazoles; REDUCTIVE MINISCI REACTION; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; CATALYST-FREE; METAL; QUINOXALIN-2(1H)-ONES; HYDROXYLATION; DERIVATIVES; OXIDATION; DESIGN;
D O I
10.1016/j.cclet.2020.02.011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1895 / 1898
页数:4
相关论文
共 79 条
[1]   Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones [J].
Bao, Pengli ;
Liu, Fei ;
Lv, Yufen ;
Yue, Huilan ;
Li, Jiang-Sheng ;
Wei, Wei .
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) :492-498
[2]   Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran [J].
Bao, Wen-Hu ;
Wang, Zheng ;
Tang, Xiao ;
Zhang, Yun-Fu ;
Tan, Jia-Xi ;
Zhu, Qin ;
Cao, Zhong ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2259-2262
[3]   Visible light-mediated C-P bond formation reactions [J].
Cai, Bao-Gui ;
Xuan, Jun ;
Xiao, Wen-Jing .
SCIENCE BULLETIN, 2019, 64 (05) :337-350
[4]  
Cao G., 2013, J ORG CHEM, V38, P346
[5]   The concept of dual roles design in clean organic preparation [J].
Cao, Zhong ;
Zhu, Qin ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2132-2138
[6]   2-Aminobenzothiazole derivatives: Search for new antifungal agents [J].
Catalano, Alessia ;
Carocci, Alessia ;
Defrenza, Ivana ;
Muraglia, Marilena ;
Carrieri, Antonio ;
Van Bambeke, Francoise ;
Rosato, Antonio ;
Corbo, Filomena ;
Franchini, Carlo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 :357-364
[7]  
Daclina T.L., 2018, NEW J CHEM, V42, P776
[8]   Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids for the synthesis of 2-sulfonylquinoline via radical reactions [J].
Dong, Dao-Qing ;
Li, Li-Xia ;
Li, Guang-Hui ;
Deng, Qi ;
Wang, Zu-Li ;
Long, Shu .
CHINESE JOURNAL OF CATALYSIS, 2019, 40 (10) :1494-1498
[9]   Direct Synthesis of Sulfonated or Sulfenylated Pyrazolones Mediated by KIO3 and Their Anti -microbial Activity [J].
Dong, Daoqing ;
Chen, Wenjing ;
Chen, Demao ;
Li, Lixia ;
Li, Guanghui ;
Wang, Zuli ;
Deng, Qi ;
Long, Shu .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) :3190-3198
[10]   Copper-Catalyzed Domino Synthesis of Sulfur-Containing Heterocycles Using Carbon Disulfide as a Building Block [J].
Gan, Ziyu ;
Yan, Qiuli ;
Li, Guoqing ;
Li, Qin ;
Dou, Xiaomeng ;
Li, Guang-Yao ;
Yang, Daoshan .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) :4558-4567