Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-lodoanilines, Isocyanide, and Potassium Sulfide

被引：48
|
作者：
Dang, Pan [1 ]
Zeng, Weilan [1 ]
Liang, Yun [1 ,2 ]
机构：
[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Natl & Local Joint Engn Lab New Petrochem Mat & F, Changsha 410081, Hunan, Peoples R China
[2] Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 01期
关键词：
DERIVATIVES; EFFICIENT; ACCESS; 2-MERCAPTOBENZOTHIAZOLE; HALOANILINES; REACTIVITY;
D O I：
10.1021/ol503186w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.
引用
收藏
页码：34 / 37
页数：4
相关论文
共 50 条
  • [1] Copper catalyzed three-component synthesis of benzothiazolones from o-iodoanilines, DMF, and potassium sulfide
    Yang, Yuan
    Zhang, Xiaoyun
    Zeng, Weilan
    Huang, Hui
    Liang, Yun
    [J]. RSC ADVANCES, 2014, 4 (12): : 6090 - 6093
  • [2] Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides
    Chen, Yiding
    Murray, Philip R. D.
    Davies, Alyn T.
    Willis, Michael C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (28) : 8781 - 8787
  • [3] Copper-catalyzed, Three-component Polymerization for the Synthesis of Polyphosphonylamidines
    Wang, Wei-hu
    He, Jun-nan
    Zheng, Yu-bin
    Zheng, Nan
    [J]. ACTA POLYMERICA SINICA, 2021, 52 (09): : 1129 - 1137
  • [4] Copper-catalyzed three-component reaction for the synthesis of fluoroalkoxyl imidates
    Wang, Zeng
    Ding, Xinzhi
    Li, Shiwei
    Weng, Zhiqiang
    [J]. TETRAHEDRON, 2018, 74 (46) : 6631 - 6634
  • [5] Copper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines
    Chu, Duc
    Zoll, Adam J.
    Ellman, Jonathan A.
    [J]. ORGANIC LETTERS, 2024, 26 (22) : 4803 - 4807
  • [6] Copper-catalyzed three-component oxycyanation of alkenes
    Zeng, Yuehua
    Li, Yajun
    Lv, Daqi
    Bao, Hongli
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (05) : 908 - 914
  • [7] Copper-Catalyzed Three-Component Borylstannylation of Alkynes
    Takemoto, Yuki
    Yoshida, Hiroto
    Takaki, Ken
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (46) : 14841 - 14844
  • [8] Copper-catalyzed three-component one-pot synthesis of quinazolines
    Ju, Jia
    Hua, Ruimao
    Su, Ji
    [J]. TETRAHEDRON, 2012, 68 (46) : 9364 - 9370
  • [9] Copper-Catalyzed Three-Component Germyl Peroxidation of Alkenes
    Luo, Yani
    Xu, Boxia
    Lv, Leiyang
    Li, Zhiping
    [J]. ORGANIC LETTERS, 2022, 24 (12) : 2425 - 2430
  • [10] Copper-Catalyzed Three-Component Carboboration of Alkynes and Alkenes
    Yoshida, Hiroto
    Kageyuki, Ikuo
    Takaki, Ken
    [J]. ORGANIC LETTERS, 2013, 15 (04) : 952 - 955
12345