Eosin Y Catalyzed Visible-Light-Driven Aerobic Oxidative Cyclization of Thioamides to 1,2,4-Thiadiazoles

被引：77
作者：
Srivastava, Vishnu P. [1 ]
Yadav, Arvind K. [1 ]
Yadav, Lal Dhar S. [1 ]
机构：
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
来源：
SYNLETT | 2013年 / 24卷 / 04期
关键词：
visible light; eosin Y; photoredox; thioamides; cyclization; thiadiazoles; PHOTOREDOX CATALYSIS; 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES; DIASTEREOSELECTIVE SYNTHESIS; OXIDIZING-AGENTS; EFFICIENT; DIMERIZATION; PHOTOCATALYSIS; HETEROCYCLES; DERIVATIVES; INHIBITORS;
D O I：
10.1055/s-0032-1318158
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach for an efficient metal-free synthesis of 1,2,4-thiadiazoles from primary thioamides using visible light and air in the presence of eosin Y as a photoredox catalyst is reported. The protocol involves an aerobic oxidative cyclization of thioamides via the formation of C-N and C-S bonds to afford excellent yields of the products in a simple one-pot operation under mild conditions.
引用
收藏
页码：465 / 470
页数：6
相关论文
共 50 条
  • [41] Eosin-Y/Cu(OAc)2-catalyzed aerobic oxidative coupling reactions of glycine esters in the dark
    Chowdhury, Raghunath
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (27) : 5387 - 5392
  • [42] Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation
    Yu, Wentao
    Huang, Yubing
    Li, Jianxiao
    Tang, Xiaodong
    Wu, Wanqing
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) : 9334 - 9343
  • [43] Visible light-induced cyclization reactions for the synthesis of 1,2,4-triazolines and 1,2,4-triazoles
    Wang, Hongyu
    Ren, Yanfei
    Wang, Kaiye
    Man, Yunquan
    Xiang, Yanan
    Li, Na
    Tang, Bo
    CHEMICAL COMMUNICATIONS, 2017, 53 (69) : 9644 - 9647
  • [44] Phenanthrene Synthesis by Eosin Y-Catalyzed, Visible Light-Induced [4+2] Benzannulation of Biaryldiazonium Salts with Alkynes
    Xiao, Tiebo
    Dong, Xichang
    Tang, Yanchi
    Zhou, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (17) : 3195 - 3199
  • [45] Highly Efficient Visible-Light-Driven H2 Production via an Eosin Y-Based Metal-Organic Framework
    Wang, Jian
    Liu, Yanhong
    Li, Yang
    Xia, Lingling
    Jiang, Min
    Wu, Pengyan
    INORGANIC CHEMISTRY, 2018, 57 (13) : 7495 - 7498
  • [46] Visible-Light-Mediated Eosin Y Photoredox-Catalyzed Vicinal Thioamination of Alkynes: Radical Cascade Annulation Strategy for 2-Substituted-3-sulfenylindoles
    Tambe, Shrikant D.
    Rohokale, Rajendra S.
    Kshirsagar, Umesh A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (18) : 2117 - 2121
  • [47] Co-Catalyzed Intramolecular S-N Bond Formation in Water for 1,2-Benzisothiazol-3(2H)-ones and 1,2,4-Thiadiazoles Synthesis
    Yang, Liting
    Song, Lijuan
    Tang, Shanyu
    Li, Longjia
    Li, Heng
    Yuan, Bingxin
    Yang, Guanyu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (06) : 1281 - 1285
  • [48] Visible-Light-Driven Nitrogen Radical-Catalyzed [3+2] Cyclization of Vinylcyclopropanes and N-Tosyl Vinylaziridines with Alkenes
    Zhao, Quan-Qing
    Zhou, Xue-Song
    Xu, Shuang-Hua
    Wu, Ya-Li
    Xiao, Wen-Jing
    Chen, Jia-Rong
    ORGANIC LETTERS, 2020, 22 (06) : 2470 - 2475
  • [49] Electrochemical Synthesis of 3,5-Bis(acyl)-1,2,4-thiadiazoles through n-Bu4NI-mediated Oxidative Dimerization of α-Oxothioamides
    Shivaraj, Mahadev
    Suresh, Rajaghatta N.
    Swaroop, Toreshettahally R.
    Kumara, Manikyanahally N.
    Rangappa, Kanchugarakoppal S.
    Mantelingu, Kempegowda
    Mamatha Devi, Adaganahalli Boregowda
    Manasa, Madihalli Prasanna
    Umashankara, Muddegowda
    ELECTROCHEMISTRY, 2023, 91 (12)
  • [50] Visible-Light-Driven CO2 Reduction Catalyzed by a Dinuclear Nickel Complex
    Wang, Jia-Wei
    Sun, Jia-Kai
    Liu, Dong-Cheng
    Jiang, Long
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (47) : 4450 - 4453
12345