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
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1267卷
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
  • [1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [2] Recent development in transition metal-catalysed C-H olefination
    Ali, Wajid
    Prakash, Gaurav
    Maiti, Debabrata
    [J]. CHEMICAL SCIENCE, 2021, 12 (08) : 2735 - 2759
  • [3] [Anonymous], 2016, APEX3 VERS 2015 9
  • [4] Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent
    Campiani, G
    Aiello, F
    Fabbrini, M
    Morelli, E
    Ramunno, A
    Armaroli, S
    Nacci, V
    Garofalo, A
    Greco, G
    Novellino, E
    Maga, G
    Spadari, S
    Bergamini, A
    Ventura, L
    Bongiovanni, B
    Capozzi, M
    Bolacchi, F
    Marini, S
    Coletta, M
    Guiso, G
    Caccia, S
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) : 305 - 315
  • [5] Copper-Catalyzed Sequential C(sp2)/C(sp3)-H Amination of 2-Vinylanilines with N-Fluorobenzenesulfonimide
    Cao, Wen-Bin
    Xu, Xiao-Ping
    Ji, Shun-Jun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) : 1771 - 1776
  • [6] Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides
    Carta, A
    Loriga, M
    Paglietti, G
    Mattana, A
    Fiori, PL
    Mollicotti, P
    Sechi, L
    Zanetti, S
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (02) : 195 - 203
  • [7] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
    Cernak, Tim
    Dykstra, Kevin D.
    Tyagarajan, Sriram
    Vachal, Petr
    Krska, Shane W.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 546 - 576
  • [8] Direct Palladium-Catalyzed β-Arylation of Lactams
    Chen, Ming
    Liu, Feipeng
    Dong, Guangbin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (14) : 3815 - 3819
  • [9] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds
    Cherney, Alan H.
    Kadunce, Nathaniel T.
    Reisman, Sarah E.
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9587 - 9652
  • [10] Research Process towards the Synthesis of Pyrrolo[1,2-a]quinoxaline Compounds
    Cong, Wenxia
    Wang, Li
    Yu, Fuqiang
    Li, Jixing
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (11) : 2866 - 2878
1234567