Lewis base-catalyzed [3+2] annulation of β-oxo-acrylamides with acyl isothiocyanates: facile access to 2-iminothiazolidin-4-one derivatives

被引：2
|
作者：
Liu, Wanxing [1 ]
Mao, Zhehui [3 ]
Chong, Daohuang [3 ]
Wang, Zhaoxue [2 ]
Zhang, Keying [2 ]
Wu, Lingang [2 ,3 ]
Xie, Lei [2 ]
机构：
[1] Nonpubl Enterprise Serv Ctr Liaocheng, Liaocheng 252000, Shandong, Peoples R China
[2] Liaocheng Univ, Sch Chem & Chem Engn, Sch Pharm, Liaocheng 252000, Shandong, Peoples R China
[3] Jinan Enlighten Biotechnol Co Ltd, Jinan 250013, Shandong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2024年 / 140卷
关键词：
Acyl isothiocyanate; 3+2] annulation; 2-Iminothiazolidin-4-one; Oxo-acrylamide; SELECTIVE-INHIBITION; AZAOXYALLYL CATIONS; CYCLOADDITION; SULFUR; 5-ARYLIDENE-2-IMINO-4-THIAZOLIDINONES; DESIGN; OXYGEN;
D O I：
10.1016/j.tetlet.2024.155022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient protocol for the Cs 2 CO 3 -catalyzed [3 + 2] annulation of /3-oxo-acrylamides with acyl isothiocyanates has been developed under mild reaction conditions. This strategy offers a streamlined route to access 2-iminothiazolidin-4-one derivatives with yields of 53 -83 %. The annulation is characterized by being transition-metal-free, atom-economic, and operationally straightforward.
引用
收藏
页数：4
相关论文
共 50 条
  • [31] Co(II)-Catalyzed Desilylative Annulation of Benzamides and Acrylamides with Alkynylsilanes: Access to 3-Methyleneisoindolin-1-one and 5-Methylene-1H-pyrrol-2(5H)-one Derivatives
    Wang, Jingyu
    Teng, Qiuxun
    Lin, Cong
    Gao, Fei
    Liu, Xiuhong
    Shen, Liang
    SYNTHESIS-STUTTGART, 2020, 52 (13): : 1969 - 1980
  • [32] Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core
    Shirsat, Prashishkumar K.
    Khomane, Navnath B.
    Meshram, Sneha H.
    Sridhar, Balasubramanian
    Meshram, Harshadas M.
    Kumbhare, Ravindra M.
    SYNTHESIS-STUTTGART, 2019, 51 (06): : 1473 - 1481
  • [33] Rh(III)-Catalyzed [3+2] Annulation of Aniline Derivatives with Vinylsilanes via C-H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives
    Khake, Shrikant M.
    Chatani, Naoto
    ACS CATALYSIS, 2021, 11 (19): : 12375 - 12383
  • [34] Unusual Formal [1+4] Annulation through Tandem P(NMe2)3-Mediated Cyclopropanation/Base-Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones
    Zhou, Rong
    Zhang, Kai
    Han, Ling
    Chen, Yusong
    Li, Ruifeng
    He, Zhengjie
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (17) : 5883 - 5887
  • [35] Facile synthesis of 3-aldehyde-2-substituted thiophenes through Lewis base catalyzed [3+2] cycloaddition of 1,4-dithiane-2,5-diols with ynals
    Shi, Wenjuan
    Wan, Li
    Hu, Yimin
    Sun, Shaofa
    Li, Wenjun
    Peng, Yanhong
    Wu, Minghu
    Guo, Haibing
    Wang, Jian
    TETRAHEDRON LETTERS, 2015, 56 (16) : 2083 - 2085
  • [36] Asymmetric [3+2] annulation of N-protected isatins with but-3-yn-2-one catalyzed by DIOP: facile creation of enantioenriched spiro[furan-2,3′-indoline]-2′,4(5H)-dione
    Lian, Zhong
    Shi, Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (40) : 8048 - 8050
  • [37] Base-promoted synthesis of 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives via [3+2] annulation of 2-alkynylpyrroles with isothiocyanates
    Zhang, Ziyin
    Guo, Biao
    Zhou, Yiming
    Hua, Ruimao
    TETRAHEDRON, 2016, 72 (47) : 7613 - 7619
  • [38] Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2, 4-dienone derivatives
    Gao, Wan
    Chen, Zhong
    Yang, Yanan
    Jiang, Jianshuang
    Feng, Ziming
    Zhang, Xu
    Yuan, Xiang
    Zhang, Peicheng
    CARBOHYDRATE RESEARCH, 2019, 484
  • [39] Organocatalytic asymmetric [3+2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives
    Yu, Ji-cong
    Yu, Le-mao
    Zhao, Xiao-yun
    Gan, Lu
    Zhu, Wei-wei
    Wang, Ze-chen
    Wang, Rui
    Jiang, Xianxing
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (13): : 2040 - 2044
  • [40] Multifunctional chiral phosphine-catalyzed [3+2] annulation of Morita-Baylis-Hillman carbonates with cyclopentenones: asymmetric synthesis of 4-oxo-hexahydropentalenes
    Wang, Chang
    Gao, Zhenzhen
    Zhou, Leijie
    Wang, Qijun
    Wu, Yang
    Yuan, Chunhao
    Liao, Jianning
    Xiao, Yumei
    Guo, Hongchao
    CHEMICAL COMMUNICATIONS, 2018, 54 (03) : 279 - 282
12345