Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide

被引:19
|
作者
Zeng, Weilan [1 ]
Dang, Pan [1 ]
Zhang, Xiaoyun [1 ]
Liang, Yun [1 ]
Peng, Caiyun [2 ]
机构
[1] Hunan Normal Univ, Natl & Local Joint Engn Lab New Petrochem Mat & F, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China
[2] Hunan Univ Chinese Med, Sch Pharmaceut Sci, Changsha 410208, Hunan, Peoples R China
关键词
S BOND FORMATION; TANDEM REACTION; C-H; INTRAMOLECULAR CYCLIZATION; EFFICIENT SYNTHESIS; DIRECT AMINATION; BENZOTHIAZOLES; ISOTHIOCYANATES; HETEROARYL; CONVENIENT;
D O I
10.1039/c4ra04047c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles has been developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(II) trifluoromethanesulfonate to afford the corresponding 2-aminobenzothiazole derivatives in good to perfect yields.
引用
收藏
页码:31003 / 31006
页数:4
相关论文
共 50 条
  • [1] Novel copper-catalyzed rearrangement of 2-aminobenzothiazoles to phenothiazines
    Beresneva, T.
    Abele, E.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) : 1420 - 1422
  • [2] Novel copper-catalyzed rearrangement of 2-aminobenzothiazoles to phenothiazines
    T. Beresneva
    E. Abele
    Chemistry of Heterocyclic Compounds, 2012, 48 : 1420 - 1422
  • [3] Copper-catalyzed synthesis of 2-aminobenzothiazoles from 2-iodophenyl isocyanides, potassium sulfide and amines
    Min, Hao
    Xiao, Genhua
    Liu, Wenjuan
    Liang, Yun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (47) : 11088 - 11091
  • [4] Copper-catalyzed tandem reaction of 2-haloanilines with thiocarbamoyl chloride: Synthesis of 2-aminobenzothiazoles
    Chang, Cai-Zhu
    Xu, Wan
    Zeng, Meng-Tian
    Liu, Min
    Liu, Xing
    Zhu, Hui
    Dong, Zhi-Bing
    SYNTHETIC COMMUNICATIONS, 2017, 47 (13) : 1262 - 1267
  • [5] Copper-Catalyzed Tandem Reaction of 2-Haloaniline Derivatives with Tetraalkylthiuram Disulfides: Selective Synthesis of 2-Aminobenzothiazoles
    Pi, Sha-Sha
    Zhang, Xing-Guo
    Tang, Ri-Yuan
    Li, Jin-Heng
    SYNLETT, 2009, (18) : 3032 - 3036
  • [6] Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles
    Saha, Prasenjit
    Ramana, Tamminana
    Purkait, Nibadita
    Ali, Md Ashif
    Paul, Rajesh
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22): : 8719 - 8725
  • [7] Ligand- and solvent-free synthesis of 2-aminobenzothiazoles by copper-catalyzed tandem reaction of 2-haloanilines with isothiocyanates
    Yao, Ruiya
    Liu, Haiyi
    Wu, Yichao
    Cai, Mingzhong
    APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (02) : 109 - 113
  • [8] Copper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines
    Qiu, Jing-Wen
    Hu, Bo-Lun
    Zhang, Xing-Guo
    Tang, Ri-Yuan
    Zhong, Ping
    Li, Jin-Heng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 3122 - 3127
  • [9] Copper(II)-Promoted Cascade Synthesis of 2-Aminobenzothiazoles Starting from 2-Iodoanilines and Sodium Dithiocarbamates
    Zhu, Hui
    Zhang, Shi-Bo
    Liu, Xing
    Cheng, Yu
    Peng, Han-Ying
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (41) : 5711 - 5716
  • [10] Progress in the Synthesis of 2-Aminobenzothiazoles
    Hou, Qiufei
    Zhang, Rui
    Liang, Jiemei
    Yao, Weizhong
    Cheng, Hua
    Chen, Cheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1498 - 1526