A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

被引:0
|
作者
Wang, Mingxu [1 ]
Gong, Yuchen [1 ]
Shi, Yaolian [1 ]
Zhao, Qihai [1 ]
Zhao, Xiao-Jing [1 ]
Li, Ganpeng [1 ]
He, Yonghui [1 ]
机构
[1] Yunnan Minzu Univ, Sch Ethn Med, Key Lab Chem Ethn Med Resources, Key Lab Nat Prod Synthet Biol Ethn Med Endophytes, Kunming 650500, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期
关键词
ELECTROCHEMICAL SYNTHESIS; STRATEGIES; CHEMISTRY;
D O I
10.1021/acs.joc.4c01800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3H)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.
引用
收藏
页码:17778 / 17788
页数:11
相关论文
共 50 条
  • [31] Copper Nitrate Mediated Regioselective [2+2+1] Cyclization of Alkynes with Alkenes: A Cascade Approach to 2-Isoxazolines
    Gao, Mingchun
    Li, Yingying
    Gan, Yuansheng
    Xu, Bin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8795 - 8799
  • [32] FT-IR, HF and DFT structural, vibrational analysis of 5-chloro-3-(2-(4-ethylpiperazin-1-yl)-2-oxoethyl)benzo[d]thiazol-2(3H)-one molecule
    Tasal, Erol
    Kumalar, Mustafa
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 124 : 687 - 696
  • [33] The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
    Wu, Deng-Ze
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2019, 234 (06): : 1225 - 1226
  • [34] Synthesis, Biological Evaluation and in Silico Studies of New Pyrazoline Derivatives Bearing Benzo[d]thiazol-2(3H)-one Moiety as Potential Urease Inhibitors
    Tok, Fatih
    Baltas, Nimet
    Tatar, Gizem
    Kocyigit-Kaymakcioglu, Bedia
    CHEMISTRY & BIODIVERSITY, 2022, 19 (03)
  • [35] ADDITION OF DIETHYL MESOXALATE TO BENZOFURANE-2(3H)-ONE, 1-BENZOTHIOPHENE-2(3H)-ONE AND 2-INDOLINONE
    WOLFERS, H
    KRAATZ, U
    KORTE, F
    HETEROCYCLES, 1975, 3 (07) : 571 - 573
  • [36] 1,6,6-trimethyl-1H-chromeno[6,7-d]thiazol-2(6H)-one
    Tang, Jian
    Wang, Yang
    Zhang, Bei-Na
    Xia, Peng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O891 - U2376
  • [37] Synthesis and study on the binding of thiazol-2(3H)-ylidine derivative with human serum albumin using spectroscopic and molecular docking methods
    Hassan, Mohammad Fahimul
    Rauf, Abdul
    LUMINESCENCE, 2017, 32 (04) : 602 - 611
  • [38] 1-Octyl-1H-benzimidazol-2(3H)-one
    Belaziz, Dounia
    Rodi, Youssef Kandri
    Essassi, El Mokhtar
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1276 - +
  • [39] 1-Nonyl-1H-benzimidazol-2(3H)-one
    Ouzidan, Younes
    Rodi, Youssef Kandri
    Butcher, Raymond J.
    Essassi, El Mokhtar
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O283 - U2037
  • [40] 1-Benzyl-1H-benzimidazol-2(3H)-one
    Ouzidan, Younes
    Essassi, El Mokhtar
    Luis, Santiago V.
    Bolte, Michael
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1822 - U1837