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
  • [31] Knowles D. B., 2008, CHEM ABSTR, V150, P86349
  • [32] A3 receptors in cortical neurons:: Pharmacological aspects and neuroprotection during hypoxia
    Lewerenz, A
    Hentschel, S
    Vissiennon, Z
    Michael, S
    Nieber, K
    [J]. DRUG DEVELOPMENT RESEARCH, 2003, 58 (04) : 420 - 427
  • [33] Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions
    Liu, Chao
    Zhang, Hua
    Shi, Wei
    Lei, Aiwen
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1780 - 1824
  • [34] Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions
    Lyons, Thomas W.
    Sanford, Melanie S.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 1147 - 1169
  • [35] Cu(II)-mediated oxidative intermolecular ortho C-H functionalisation using tetrahydropyrimidine as the directing group
    Mizuhara, Tsukasa
    Inuki, Shinsuke
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    [J]. CHEMICAL COMMUNICATIONS, 2009, (23) : 3413 - 3415
  • [36] Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding
    Nandwana, Nitesh Kumar
    Pericherla, Kasiviswanadharaju
    Kaswan, Pinku
    Kumar, Anil
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2947 - 2950
  • [37] Odani R., 2014, ANGEW CHEM, V126, P10960
  • [38] Copper-Mediated C6-Selective Dehydrogenative Heteroarylation of 2-Pyridones with 1,3-Azoles
    Odani, Riko
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10784 - 10788
  • [39] Antibacterial activity of quinoxalines, quinazolines, and 1,5-naphthyridines
    Parhi, Ajit K.
    Zhang, Yongzheng
    Saionz, Kurt W.
    Pradhan, Padmanava
    Kaul, Malvika
    Trivedi, Kalkal
    Pilch, Daniel S.
    LaVoie, Edmond J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (17) : 4968 - 4974
  • [40] Park T. Y., 2010, CHEM ABSTR, V153