Direct synthesis of polysubstituted 2-aminothiophenes by Cu(II)-catalyzed addition/oxidative cyclization of alkynoates with thioamides

被引：27
|
作者：
Ge, Li-Shi [1 ]
Wang, Zheng-Lin [1 ]
An, Xing-Lan [1 ]
Luo, Xiaoyan [1 ]
Deng, Wei-Ping [1 ]
机构：
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 42期
关键词：
ONE-POT SYNTHESIS; HIGHLY SUBSTITUTED THIOPHENES; CATALYZED AMINATION; EFFICIENT SYNTHESIS; COPPER(I)-CATALYZED SYNTHESIS; PHARMACOLOGICAL EVALUATION; 1,3-DICARBONYL COMPOUNDS; ANTIINFLAMMATORY AGENTS; BETA-KETOTHIOAMIDES; S-ALKENYLATION;
D O I：
10.1039/c4ob01534g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile and direct synthetic method was developed for the construction of structurally important 2-aminothiophenes in moderate to excellent yields (up to 91%), via Cu(II)-catalyzed addition/oxidative cyclization of readily available thioamides with alkynoates under an air atmosphere.
引用
收藏
页码：8473 / 8479
页数：7
相关论文
共 50 条
  • [1] Chemo- and regioselective synthesis of polysubstituted 2-aminothiophenes by the cyclization ofgem-dibromo orgem-dichloroalkenes with β-keto tertiary thioamides
    Zhang, Xuxue
    Liu, Chuan
    Deng, Yupian
    Cao, Song
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (38) : 7540 - 7544
  • [2] Synthesis of N,N-disubstituted 2-aminothiophenes by the cyclization of gem-difluoroalkenes with β-keto thioamides
    Zhang, Xuxue
    Wu, Mingsheng
    Zhang, Juan
    Cao, Song
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (11) : 2436 - 2442
  • [3] Direct synthesis of β-alkenylpyrroles by Pd(II)-catalyzed addition of pyrroles to alkynoates
    Oyamada, J
    Lu, WJ
    Jia, CG
    Kitamura, T
    Fujiwara, Y
    [J]. CHEMISTRY LETTERS, 2002, (01) : 20 - 21
  • [4] NOVEL SYNTHESIS OF 2-AMINOTHIOPHENES VIA IODOIMINOTHIOLACTONIZATION OF GAMMA-DELTA-UNSATURATED SECONDARY THIOAMIDES
    TAKAHATA, H
    MORIYAMA, K
    MARUYAMA, M
    YAMAZAKI, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (22) : 1671 - 1671
  • [5] Synthetic Approach to Polysubstituted Furans: An Efficient Addition/Oxidative Cyclization of Alkynoates and 1,3-Dicarbonyl Compounds
    Liu, Weibing
    Jiang, Huanfeng
    Zhang, Min
    Qi, Chaorong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03): : 966 - 968
  • [6] Photocatalytic oxidative cyclization of aromatic thioamides catalyzed by Cu2O rhombic dodecahedra
    Wang, Guan-Ru
    Huang, Michael H.
    [J]. JOURNAL OF MATERIALS CHEMISTRY A, 2024, 12 (23) : 13792 - 13799
  • [7] An efficient synthesis of 2-aminothiophenes via the Gewald reaction catalyzed by enzymes in ionic liquids
    Zeng, Qingtao
    Hui, Yonghai
    Wang, Yuting
    Wen, Keshu
    Huang, Jiangchi
    Zhang, Yongfei
    Wang, Yun
    Zhang, Shiqi
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2023, 1294
  • [8] Synthesis of polysubstituted quinolines via copper(II)-catalyzed annulation of 2-aminoaryl ketones with alkynoates
    Bagdi, Avik Kumar
    Santra, Sougata
    Rahman, Matiur
    Majee, Adinath
    Hajra, Alakananda
    [J]. RSC ADVANCES, 2013, 3 (46): : 24034 - 24037
  • [9] Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate
    Hu, Y
    Chen, ZC
    Le, ZG
    Zheng, QG
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (20) : 3801 - 3806
  • [10] Phosphine-catalyzed annulation of thioamides and 2-alkynoates: A new synthesis of thiazolines
    Liu, B
    Davis, R
    Joshi, B
    Reynolds, DW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13): : 4595 - 4598
12345