One-Pot Synthesis of Triazoloquinazolinones via Copper-Catalyzed Tandem Click and Intramolecular C-H Amidation

被引:38
|
作者
Selvaraju, Manikandan [1 ]
Sun, Chung-Ming [1 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
关键词
CH amidation; copper-catalyzed reaction; one-pot protocol; tandem reactions; triazoloquinazolinones; DIRECT ARYLATIONS; DIRECT AMINATION; ORGANIC AZIDES; DIVERSITY; LIGATION;
D O I
10.1002/adsc.201301013
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel and highly efficient copper-catalyzed tandem synthesis of triazoloquinazolinones is explored. The synthetic strategy involves a sequential one-pot click reaction followed by aerobic intramolecular CH amidation. Two distinct and important transformations were carried out in one-pot by employing a single cost-effective copper catalyst. The milder, rapid and ligand-free reaction conditions as well as a broader substrate scope are the salient features of this novel protocol.
引用
收藏
页码:1329 / 1336
页数:8
相关论文
共 50 条
  • [1] Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation
    Gu, Jiajia
    Fang, Zheng
    Yang, Yuhang
    Yang, Zhao
    Wan, Li
    Li, Xin
    Wei, Ping
    Guo, Kai
    RSC ADVANCES, 2016, 6 (92) : 89413 - 89416
  • [2] Copper-Catalyzed One-Pot Synthesis of Imidazo/Benzoimidazoquinazolinones by Sequential Ullmann-Type Coupling and Intramolecular C-H Amidation
    Xu, Hao
    Fu, Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (04) : 1180 - 1186
  • [3] Copper-catalyzed one-pot synthesis of propargylamines via C-H activation in PEG
    Zhang, Qiang
    Chen, Jiu-Xi
    Gao, Wen-Xia
    Ding, Jin-Chang
    Wu, Hua-Yue
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (11) : 809 - 812
  • [4] One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C-H Amidation Process
    Waddella, Lachlan J. N.
    Henry, Martyn C.
    Mostafa, Mohamed A. B.
    Sutherland, Andrew
    SYNTHESIS-STUTTGART, 2022, 54 (20): : 4551 - 4560
  • [5] One-pot synthesis of polyfunctionalized quinolines via a copper-catalyzed tandem cyclization
    Chen, Dianpeng
    Sun, Xuejun
    Shan, Yingying
    You, Jinmao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (41) : 7657 - 7662
  • [6] Copper-catalyzed N-arylation and aerobic oxidative C-H/C-H coupling: one-pot synthesis of indoloimidazoquinoline derivatives
    Wang, Meng
    Jin, Yunhe
    Yang, Haijun
    Fu, Hua
    Hu, Liming
    RSC ADVANCES, 2013, 3 (22) : 8211 - 8214
  • [7] Copper-catalyzed one-pot oxidative amidation between methylarenes and amines
    Yang, Yuhang
    Gu, Jiajia
    Fang, Zheng
    Yang, Zhao
    Wei, Ping
    Guo, Kai
    RSC ADVANCES, 2017, 7 (37) : 22797 - 22801
  • [8] Copper-catalyzed one-pot synthesis of alkynylphophonates
    Song, Wang-Ze
    Li, Jun-Hao
    Li, Ming
    He, Jun-Nan
    Dong, Kun
    Ullah, Karim
    Zheng, Yu-Bin
    SYNTHETIC COMMUNICATIONS, 2019, 49 (05) : 697 - 703
  • [9] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [10] Copper-catalyzed oxidative amidation of dibenzylamines via C-H bond activation
    Hu, Jinjin
    Zuo, Xiujin
    Huang, Hanmin
    CHINESE JOURNAL OF CATALYSIS, 2013, 34 (09) : 1644 - 1650