Iron-Catalyzed Synthesis of Substituted Thiazoles from Enamines and Elemental Sulfur through C-S Bond Formation

被引:48
|
作者
Wu, Mingzhong [1 ]
Jiang, Yong [2 ]
An, Zhenyu [1 ]
Qi, Zhenjie [1 ]
Yan, Rulong [1 ]
机构
[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou, Gansu, Peoples R China
[2] Yangtze Normal Univ, Sch Chem & Chem Engn, Chongqing, Peoples R China
基金
中国国家自然科学基金;
关键词
Thiazoles; enamines; elemental sulfur; C-S bond; METAL-FREE CONDITIONS; REDOX CONDENSATION REACTION; SULFONYL HYDRAZIDES; HOMOPROPARGYLIC ALCOHOLS; O-HALONITROBENZENES; DIRECT THIOLATION; NATURAL-PRODUCTS; FACILE SYNTHESIS; MILD CONDITIONS; 3-COMPONENT;
D O I
10.1002/adsc.201800693
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An atom economical approach for the synthesis of substituted thiazoles starting from enamines and elemental sulfur through the C-H functionalization/C-S bond formation is described. Under the optimized conditions, various substituted enamines reacted smoothly with elemental sulfur and the desired substituted thiazoles were generated in moderate to excellent yields.
引用
收藏
页码:4236 / 4240
页数:5
相关论文
共 50 条
  • [1] Metal-Free C-S Bond Formation in Elemental Sulfur and Cyclobutanol Derivatives: The Synthesis of Substituted Thiophenes
    Wu, Mingzhong
    Yan, Chaoxian
    Zhuang, Daijiao
    Yan, Rulong
    ORGANIC LETTERS, 2022, 24 (29) : 5309 - 5313
  • [2] Double C-S bond formation via C-H bond functionalization: synthesis of benzothiazoles and naphtho[2,1-d] thiazoles from N-substituted arylamines and elemental sulfur
    Zhu, Xiaoming
    Yang, Yuzhong
    Xiao, Genhua
    Song, Jianxin
    Liang, Yun
    Deng, Guobo
    CHEMICAL COMMUNICATIONS, 2017, 53 (87) : 11917 - 11920
  • [3] Metal-catalyzed C-S bond formation using sulfur surrogates
    Sundaravelu, Nallappan
    Sangeetha, Subramani
    Sekar, Govindasamy
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (07) : 1459 - 1482
  • [4] Iron-catalyzed aerobic difunctionalization of alkenes: a highly efficient approach to construct oxindoles by C-S and C-C bond formation
    Shen, Tao
    Yuan, Yizhi
    Song, Song
    Jiao, Ning
    CHEMICAL COMMUNICATIONS, 2014, 50 (31) : 4115 - 4118
  • [5] Gold-Catalyzed Intermolecular C-S Bond Formation: Efficient Synthesis of α-Substituted Vinyl Sulfones
    Xi, Yumeng
    Shi, Xiaodong Michael
    SYNLETT, 2014, 25 (16) : A132 - A135
  • [6] Gold-Catalyzed Intermolecular C-S Bond Formation: Efficient Synthesis of α-Substituted Vinyl Sulfones
    Xi, Yumeng
    Shi, Xiaodong Michael
    SYNTHESIS-STUTTGART, 2014, 46 (19): : A132 - A135
  • [7] Iron(III)-Catalyzed Aerobic Oxidation and Cleavage/Formation of a C-S Bond
    Shi, Xiaokang
    Ren, Xiaoyu
    Ren, Zhiyong
    Li, Jian
    Wang, Yuling
    Yang, Sizhuo
    Gu, Jixiang
    Gao, Qiang
    Huang, Guosheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (23) : 5083 - 5088
  • [8] Palladium-Catalyzed C-S Bond Formation of Stable Enamines with Arene/Alkanethiols: Highly Regioselective Synthesis of β-Amino Sulfides
    Jiang, Yaojia
    Liang, Gaohui
    Zhang, Cong
    Loh, Teck-Peng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3326 - 3330
  • [9] Gold-catalyzed C-S bond formation from thiols
    Jean, Mickael
    Renault, Jacques
    van de Weghe, Pierre
    Asao, Naoki
    TETRAHEDRON LETTERS, 2010, 51 (02) : 378 - 381
  • [10] Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles
    Bose, D. Subhas
    Idrees, Mohd
    SYNTHESIS-STUTTGART, 2010, (12): : 1983 - 1988