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
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   Recent development in transition metal-catalysed C-H olefination [J].
Ali, Wajid ;
Prakash, Gaurav ;
Maiti, Debabrata .
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 [J].
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 .
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 [J].
Cao, Wen-Bin ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
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 [J].
Carta, A ;
Loriga, M ;
Paglietti, G ;
Mattana, A ;
Fiori, PL ;
Mollicotti, P ;
Sechi, L ;
Zanetti, S .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (02) :195-203
[7]   The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].
Cernak, Tim ;
Dykstra, Kevin D. ;
Tyagarajan, Sriram ;
Vachal, Petr ;
Krska, Shane W. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576
[8]   Direct Palladium-Catalyzed β-Arylation of Lactams [J].
Chen, Ming ;
Liu, Feipeng ;
Dong, Guangbin .
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 [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652
[10]   Research Process towards the Synthesis of Pyrrolo[1,2-a]quinoxaline Compounds [J].
Cong, Wenxia ;
Wang, Li ;
Yu, Fuqiang ;
Li, Jixing .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (11) :2866-2878