Electrochemical regioselective methylthiolation of imidazo[2,1-b]thiazoles with DMSO

被引:0
|
作者
Xiao, Meng [1 ]
Yi, Liyu [1 ]
Liu, Wenjie [1 ,2 ]
Cao, Gao [1 ,2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou, Peoples R China
[2] Guangdong Cosmet Engn & Technol Res Ctr, Guangzhou, Peoples R China
关键词
DMSO; electrochemistry; imidazo[2; 1-b]thiazoles; methylthiolation; regioselectivity; DIMETHYL-SULFOXIDE; SULFUR; ACTIVATION; IMIDAZOPYRIDINES; THIOMETHYLATION; SULFENYLATION; DERIVATIVES; BENZAMIDES; AMINATION; ANTITUMOR;
D O I
10.1080/00397911.2025.2453872
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
With DMSO both as the source of -SMe unit and solvent, an efficient and green electrochemical methylthiolation reaction of imidazo[2,1-b]thiazoles was developed. The transformation was performed at room temperature in 8 h under external transition metal- and oxidant-free condition. Moreover, the 2,3-dihydroimidazo[2,1-b]thiazoles and 2-phenylbenzo[d]imidazo[2,1-b]thiazole also proceeded smoothly. This strategy provides C-5 methylthiolation products with broad scope in 73-91% yields.
引用
收藏
页码:338 / 349
页数:12
相关论文
共 50 条
  • [1] Synthesis of Several Imidazo[2,1-b]thiazoles
    Bratulescu, George
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (01) : 350 - 352
  • [2] Synthetic access to imidazo[2,1-b]thiazoles
    Mohamed, Hanan A.
    Abdel-Wahab, Bakr F.
    JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (05) : 589 - 604
  • [3] Regioselective palladium-catalyzed phosphonation of imidazo[2,1-b]thiazoles with dialkyl phosphites
    Liu, Wenjie
    Wang, Shaohua
    Yao, Huagang
    Li, Ziying
    Huang, Yanling
    Kong, Chunyun
    TETRAHEDRON LETTERS, 2015, 56 (44) : 6100 - 6103
  • [4] A one-pot regioselective synthesis of benzo[d]imidazo[2,1-b]thiazoles
    Zhang, Xinhai
    Jia, Jiong
    Ma, Chen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (39) : 7944 - 7948
  • [5] Copper-Catalyzed Regioselective C5 Sulfenylation of Imidazo[2,1-b]thiazoles with Thiols
    Liu, Wenjie
    Wang, Shaohua
    Jiang, Yi
    He, Peiling
    Zhang, Qi
    Cao, Hua
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (04) : 312 - 315
  • [6] Synthesis and Biological Evaluation New Imidazo[2,1-b]thiazoles
    Syed, Manjoor A.
    Yiragamreddy, Padmanabha R.
    Chandrasekhar, K. B.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 27 (04) : 329 - 338
  • [7] One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles
    Serykh, Valery Y.
    Chernysheva, Gulnur N.
    Kondrashov, Evgeniy V.
    Vashchenko, Aleksandr V.
    Smirnov, Vladimir I.
    Rozentsveig, Igor B.
    ARKIVOC, 2015, : 377 - 391
  • [8] Microwave-assisted and catalyst-free sulfenylation of imidazo[2,1-b]thiazoles with sulfonyl hydrazides in water
    Wang, Shaohua
    Luo, Run
    Guo, Lina
    Zhu, Tianxi
    Chen, Xu
    Liu, Wenjie
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 195 (10) : 805 - 811
  • [9] Synthesis of imidazo[2,1-b]thiazoles through the reaction of thiohydantoins and α-bromoketones
    Ghanbari, Mohammad M.
    Yavari, Issa
    Emadi, Abedin
    JOURNAL OF SULFUR CHEMISTRY, 2014, 35 (01) : 57 - 61
  • [10] Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety
    Sebastian Barradas, Jose
    Ines Errea, Maria
    Beatriz D'Accorso, Norma
    CARBOHYDRATE RESEARCH, 2012, 355 : 79 - 86