Palladium-Catalyzed C(sp2)-H Activation for the Formation of C-N Bonds: Rapid Access to Benzimidazoquinazolines

被引:12
作者
Guo, Xiaolong [1 ]
Hu, Jing [1 ]
Zhang, Mengmeng [1 ]
Wang, Luyao [1 ]
机构
[1] Capital Normal Univ, Dept Chem, Beijing 100048, Peoples R China
基金
北京市自然科学基金;
关键词
benzimidazoles; palladium; C-H activation; C-N coupling; benzimidazoquinazolines; DIRECTING GROUP; COPPER; FUNCTIONALIZATION; DERIVATIVES; INHIBITORS; QUINAZOLINES; CHEMISTRY; ARYLATION; DESIGN;
D O I
10.1002/ajoc.201800710
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and effective method for Pd-catalyzed cross-dehydrogenative C(sp(2))-H/N-H couplings to synthesize fused N-heterocyclic benzimidazoquinazoline derivatives was developed. The reaction employs Pd(OAc)(2) as the catalyst and Cu(OAc)(2) or O-2 (from the air) as the terminal oxidant. The strategy uses simple and easily accessible substrates. This method provides a route to azole-fused heterocycles.
引用
收藏
页码:417 / 421
页数:5
相关论文
共 51 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] Palladium catalyzed C3-arylation of 4-hydroxy-2-pyridones
    Anagnostaki, Elissavet E.
    Fotiadou, Anna D.
    Demertzidou, Vera
    Zografos, Alexandros L.
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (52) : 6879 - 6882
  • [3] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666
  • [4] [Anonymous], ANGEW CHEM
  • [5] Recent developments on proton conducting poly(2,5-benzimidazole) (ABPBI) membranes for high temperature polymer electrolyte membrane fuel cells
    Asensio, JA
    Gómez-Romero, P
    [J]. FUEL CELLS, 2005, 5 (03) : 336 - 343
  • [6] Design, synthesis, SAR, and biological evaluation of highly potent benzimidazole-spaced phosphono-α-amino acid competitive NMDA antagonists of the AP-6 type
    Baudy, RB
    Fletcher, H
    Yardley, JP
    Zaleska, MM
    Bramlett, DR
    Tasse, RP
    Kowal, DM
    Katz, AH
    Moyer, JA
    Abou-Gharbia, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) : 1516 - 1529
  • [7] Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
  • [8] HINCKDENTINE-A - A NOVEL ALKALOID FROM THE MARINE BRYOZOAN HINCKSINOFLUSTRA-DENTICULATA
    BLACKMAN, AJ
    HAMBLEY, TW
    PICKER, K
    TAYLOR, WC
    THIRASASANA, N
    [J]. TETRAHEDRON LETTERS, 1987, 28 (45) : 5561 - 5562
  • [9] Copper-catalyzed C-N coupling/C-H functionalization: A tandem approach to azole-fused quinazoline derivatives
    Chen, Dingben
    Huang, Ling
    Yang, Jianguo
    Ma, Junna
    Zheng, Yingying
    Luo, Yi
    Shen, Yang
    Wu, Jiashou
    Feng, Chao
    Lv, Xin
    [J]. TETRAHEDRON LETTERS, 2018, 59 (21) : 2005 - 2009
  • [10] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers
    Chen, Fa-Jie
    Zhao, Sheng
    Hu, Fang
    Chen, Kai
    Zhang, Qi
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    [J]. CHEMICAL SCIENCE, 2013, 4 (11) : 4187 - 4192