Copper catalyzed aerobic oxidative amination of 3,4-dihydroquinoxalin-2(1H)-ones

被引：5
|
作者：
Wan, Shuocheng [1 ]
Wang, Jie [1 ]
Huo, Congde [1 ]
机构：
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Int Sci & Technol Cooperat, Base Water Retent Chem Funct Mat, Lanzhou 730070, Gansu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2021年 / 78卷
基金：
中国国家自然科学基金;
关键词：
Aerobic; Amination; Oxidation; Copper; 3-Aminoquinoxalinones; 3,4-Dihydroquinoxalin-2(1H)-ones; QUINOXALINE DERIVATIVES; BOND FORMATION; INHIBITORS; DESIGN;
D O I：
10.1016/j.tetlet.2021.153271
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper catalyzed aerobic sp(3) C-H amination of 3,4-dihydroquinoxalin-2(1H)-ones is developed. This protocol provides a concise method to access 3-aminoquinoxalinone derivatives with good functional-group tolerances, utilizing primary and secondary aliphatic amines as nitrogen sources under mild and simple reaction conditions. It provides a practical approach to the synthesis of pharmaceutical active 3-aminoquinoxalinones. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [31] Heteropoly acid catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones
    Maradur, Sanjeev P.
    Gokavi, Gavisiddappa S.
    CATALYSIS COMMUNICATIONS, 2007, 8 (03) : 279 - 284
  • [32] Copper-Catalyzed Aerobic Oxidative Amination of sp3C-H Bonds: Efficient Synthesis of 2-Hetarylquinazolin-4(3H)-ones
    Li, Qiang
    Huang, Yao
    Chen, Tieqiao
    Zhou, Yongbo
    Xu, Qing
    Yin, Shuang-Feng
    Han, Li-Biao
    ORGANIC LETTERS, 2014, 16 (14) : 3672 - 3675
  • [33] Copper-catalyzed C3-amination of quinoxalin-2(1H)-ones: Using Selectfluor as a mild oxidant
    Pei, Congcong
    Chen, Xiaoyu
    Li, Linlin
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2021, 83
  • [34] Copper-catalyzed aerobic cascade reaction for the conversion of 3,4-dihydropyrimidine-2(1H)-thiones to arylthiopyrimidines
    Lee, Ok Suk
    Lee, HyunKyung
    Kim, Hyejee
    Shin, Hyunik
    Sohn, Jeong-Hun
    TETRAHEDRON, 2015, 71 (19) : 2936 - 2944
  • [35] The reactions of 3-ethoxycarbonylmethylene-3,4-dihydroquinoxalin-2(1H)-one and its derivatives in the synthesis of benzodiazepines and benzimidazoles: reinvestigation, structural reassignment, and new insight
    Mamedov, Vakhid A.
    Murtazina, Anna M.
    Zhukova, Nataliya A.
    Beschastnova, Tat'yana N.
    Rizvanov, Il'dar Kh.
    Latypov, Shamil K.
    TETRAHEDRON, 2014, 70 (41) : 7567 - 7576
  • [36] Copper-Catalyzed Aryltrifluoromethylation of N-Phenylcinnamamides: Access to Trifluoromethylated 3,4-Dihydroquinolin-2(1H)-ones
    Wang, Qiang
    Han, Guifang
    Liu, Yuxiu
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2464 - 2468
  • [37] (Z)-3-(Quinolin-2-ylmethylene)-3,4-dihydroquinoxalin-2(1H)-one derivatives: AIE-active compounds with pronounced effects of ESIPT and TICT
    Yao, Qi-Chao
    Lu, Xiao-Lin
    Xia, Min
    NEW JOURNAL OF CHEMISTRY, 2014, 38 (06) : 2693 - 2700
  • [38] Copper Nitrate Catalyzed Three-Component One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones
    Wang, Min
    Jiang, Heng
    Song, Zhiguo
    Gong, Hong
    PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, 2009, 39 (04): : 372 - 379
  • [39] Copper(II) trifluoroacetate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions
    Song, Dailei
    Wang, Runxia
    Chen, Yongli
    Zhang, Shaohua
    Liu, Chunsheng
    Luo, Genxiang
    REACTION KINETICS AND CATALYSIS LETTERS, 2008, 95 (02): : 385 - 390
  • [40] Oxidative Aromatization of 3,4-Dihydroquinolin-2(1H)-ones to Quinolin-2(1H)-ones Using Transition-Metal-Activated Persulfate Salts
    Chen, Weiming
    Sun, Changliang
    Zhang, Yan
    Hu, Tianwen
    Zhu, Fuqiang
    Jiang, Xiangrui
    Abame, Melkamu Alemu
    Yang, Feipu
    Suo, Jin
    Shi, Jing
    Shen, Jingshan
    Aisa, Haji A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (13): : 8702 - 8709
12345