Copper-promoted C1-H amination of pyrrolo[1,2-a]quinoxaline with N-fluorobenzenesulfonimide

被引:9
作者
Hao, Di [1 ]
Yang, Zhen [1 ]
Liu, Yali [1 ]
Li, Yang [1 ]
Liu, Yan [1 ]
Liu, Ping [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi City 832004, Peoples R China
基金
中国国家自然科学基金;
关键词
Pyrrolo[1; 2-a ]quinoxaline; N – fluorobenzenesulfonimide; C-Hamination; VITRO ANTIMALARIAL ACTIVITY; IN-VITRO; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; FLUORINATION; IMIDATION;
D O I
10.1016/j.molstruc.2022.133636
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A copper-promoted direct C1-amination of pyrrolo[1,2-a]quinoxalines with N-fluorobenzenesulfonimide (NFSI) has been achieved. A series of C1-aminated pyrrolo[1,2-a]quinoxalines were obtained with broad substrate scope and good functional group tolerance. Gram-scale synthesis and further derivation of this aminated product were also investigated. Mechanism studies suggest that this reaction probably under-goes a free-radical process.(c) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数:6
相关论文
共 66 条
  • [31] Copper-Catalyzed Remote C-H Functionalizations of Naphthylamides through a Coordinating Activation Strategy and Single-Electron-Transfer (SET) Mechanism
    Li, Jun-Ming
    Wang, Yong-Heng
    Yu, Yang
    Wu, Rui-Bo
    Weng, Jiang
    Luo, Gui
    [J]. ACS CATALYSIS, 2017, 7 (04): : 2661 - 2667
  • [32] Simple and green synthesis of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov heterocycle rearrangement
    Li, Shichen
    Feng, Lei
    Ma, Chen
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (21) : 9320 - 9323
  • [33] Cu-catalyzed direct C1-H trifluoromethylation of pyrrolo[1,2-a] quinoxalines
    Li, Yang
    Liu, Yali
    Hao, Di
    Li, Chuntian
    Liu, Yan
    Gu, Yanlong
    Vaccaro, Luigi
    Liu, Ping
    [J]. TETRAHEDRON, 2022, 105
  • [34] Cu-catalyzed direct C1-H difluoromethylation of pyrrolo[1,2-a] quinoxalines
    Li, Yang
    Yang, Zhen
    Liu, Yali
    Liu, Yan
    Gu, Yanlong
    Liu, Ping
    [J]. MOLECULAR CATALYSIS, 2021, 511
  • [35] Radical aminooxygenation of alkenes with N-fluoro-benzenesulfonimide (NFSI) and TEMPONa
    Li, Yi
    Hartmann, Marcel
    Daniliuc, Constantin Gabriel
    Studer, Armido
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (26) : 5706 - 5709
  • [36] Introduction of Fluorine and Fluorine-Containing Functional Groups
    Liang, Theresa
    Neumann, Constanze N.
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) : 8214 - 8264
  • [37] Bifunctional acidic ionic liquid-catalyzed decarboxylative cascade synthesis of quinoxalines in water under ambient conditions
    Liu, Shanshan
    Zhang, Pingjun
    Zhang, Yuanyuan
    Zhou, Xianying
    Liang, Jiahui
    Nan, Jiang
    Ma, Yangmin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (20) : 5858 - 5865
  • [38] Ligand-Controlled Regioselective Pd-Catalyzed Diamination of Alkenes
    Liu, Xiaojian
    Hou, Chuanqi
    Peng, Yiyuan
    Chen, Pinhong
    Liu, Guosheng
    [J]. ORGANIC LETTERS, 2020, 22 (23) : 9371 - 9375
  • [39] Solvent Mediated Selective C-H Bond Iodiation Pyrrolo[1, 2-a]quinoxaline
    Liu, Yali
    Yang, Zhen
    Li, Yang
    Liu, Yan
    Liu, Ping
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4789 - 4797
  • [40] Highly selective C3-H iodination of pyrrolo[1,2-a]quinoxalines
    Liu, Yali
    Wei, Yu
    Yang, Zhen
    Li, Yang
    Liu, Yan
    Liu, Ping
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (23) : 5191 - 5196