Amides Activation: Transition Metal-Free Coupling Between C-N Activated Amides and Enolizable Amides

被引:18
|
作者
Joseph, Devaneyan [1 ]
Oh, Min Seok [1 ]
Jayaraman, Aravindan [1 ]
Lee, Sunwoo [1 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea
关键词
Amide; Metal-free; Coupling; Condensation; beta-Ketoamide; H BOND-CLEAVAGE; CATALYZED TRANSAMIDATION; EFFICIENT CATALYST; CARBOXAMIDES; KETONES;
D O I
10.1002/bkcs.12371
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition metal-free Claisen-type condensation between two different amides was developed. N-phenyl-N-tosylbenzamide derivatives reacted with enolizable amides such as N-methyl pyrrolidinone and N,N-dimethyl acetamide in the presence of NaHMDS to give their corresponding beta-ketoamides with moderate-to-good yields.
引用
收藏
页码:1293 / 1295
页数:3
相关论文
共 50 条
  • [31] Transamidation of N-Benzyl-N-Boc-amides under Transition Metal-Free and Base-Free Conditions
    Ye, Danfeng
    Chen, Hao
    Liu, Zhiyuan
    Lei, Chuanhu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1658 - 1669
  • [32] Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
    Yu, Pei
    Wang, Yuwei
    Zeng, Zhigang
    Chen, Yunfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22): : 14883 - 14891
  • [33] Internal rotation about the C-N bond of amides
    Kang, YK
    Park, HS
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2004, 676 (1-3): : 171 - 176
  • [34] Cross-Coupling of Amides by N-C Bond Activation
    Meng, Guangrong
    Shi, Shicheng
    Szostak, Michal
    SYNLETT, 2016, 27 (18) : 2530 - 2540
  • [35] AMIDES NONPLANAR SOLELY BY C-N BOND ROTATION
    COLLINS, TJ
    WORKMAN, JM
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (07): : 912 - 914
  • [36] Fe-catalyzed esterification of amides via C-N bond activation
    Chen, Xiuling
    Hu, Siying
    Chen, Rongxing
    Wang, Jian
    Wu, Minghu
    Guo, Haibin
    Sun, Shaofa
    RSC ADVANCES, 2018, 8 (09): : 4571 - 4576
  • [37] Ni-mediated C-N activation of amides and derived catalytic transformations
    Gao, Yuan
    Ji, Chong-Lei
    Hong, Xin
    SCIENCE CHINA-CHEMISTRY, 2017, 60 (11) : 1413 - 1424
  • [38] Transition metal-free N-arylation of secondary amides through iodonium salts as aryne precursors
    Wang, Ming
    Huang, Zhijian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (43) : 10185 - 10188
  • [39] Metal-Free C-H Alkyliminylation and Acylation of Alkenes with Secondary Amides
    Huang, Pei-Qiang
    Huang, Ying-Hong
    Geng, Hui
    Ye, Jian-Liang
    SCIENTIFIC REPORTS, 2016, 6
  • [40] Ni-Catalyzed Photochemical C-N Coupling of Amides with (Hetero)aryl Chlorides
    Song, Geyang
    Li, Qi
    Nong, Ding-Zhan
    Song, Jiameng
    Li, Gang
    Wang, Chao
    Xiao, Jianliang
    Xue, Dong
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (37)