Synthesis of benzimidazoles by Cu2O-catalyzed cascade reactions between o-haloaniline and amidine hydrochlorides

被引:33
|
作者
Qu, Yanyang [1 ]
Pan, Lei [1 ]
Wu, Zhiqing [1 ]
Zhou, Xiangge [1 ]
机构
[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Chengdu 610064, Peoples R China
关键词
Copper; Catalysis; Cyclization; Heterocycle; Benzimidazole; COPPER-CATALYZED SYNTHESIS; ONE-POT SYNTHESIS; COUPLING REACTIONS; PHASE SYNTHESIS; LIGANDS; ULLMANN;
D O I
10.1016/j.tet.2012.12.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Cu2O-catalyzed method for the synthesis of benzimidazole derivatives from amidine hydrochlorides and o-haloaniline has been developed. The cascade C-N coupling and intramolecular transamination reaction provided benzimidazole derivatives in high yields up to 90%. (C) 2012 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码:1717 / 1719
页数:3
相关论文
共 50 条
  • [31] Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N-H free tetrazoles with boronic acids
    Li, Yu
    Gao, Lian-Xun
    Han, Fu-She
    CHEMICAL COMMUNICATIONS, 2012, 48 (21) : 2719 - 2721
  • [32] Direct synthesis of alkynylphosphonates from alkynes and phosphite esters catalyzed by Cu/Cu2O nanoparticles supported on Nb2O5
    Yuan, Tao
    Chen, Fei
    Lu, Guo-ping
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (16) : 13957 - 13962
  • [33] Synthesis of 2-Substituted Benzimidazoles Catalyzed by FeCl3/Al2O3 Under Ultrasonic Irradiation
    Chen, Guo-Feng
    Dong, Xiao-Yun
    Meng, Fan-Zhu
    Chen, Bao-Hua
    Li, Ji-Tai
    Wang, Shu-Xiang
    Bai, Guo-Yi
    LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (07) : 464 - 469
  • [34] MgCl2•6H2O catalyzed highly efficient synthesis of 2-substituted-1H-benzimidazoles
    Ghosh, Pranab
    Subba, Raju
    TETRAHEDRON LETTERS, 2015, 56 (21) : 2691 - 2694
  • [36] INTERFACE REACTIONS BETWEEN METALS (CU, NI, AL) AND YBA2CU3O6.8
    BOHNENKAMPWEISS, R
    SCHMIDFETZER, R
    ZEITSCHRIFT FUR METALLKUNDE, 1995, 86 (04): : 261 - 269
  • [37] Cu-Pd/γ-Al2O3 catalyzed the coupling of multi-step reactions: direct synthesis of benzimidazole derivatives
    Feng, Feng
    Ye, Jia
    Cheng, Zheng
    Xu, Xiaoliang
    Zhang, Qunfeng
    Ma, Lei
    Lu, Chunshan
    Li, Xiaonian
    RSC ADVANCES, 2016, 6 (76): : 72750 - 72755
  • [38] Pd-catalyzed cascade reactions between o-iodo-N-alkenylanilines and tosylhydrazones: novel approaches to the synthesis of polysubstituted indoles and 1,4-dihydroquinolines
    Paraja, Miguel
    Valdes, Carlos
    CHEMICAL COMMUNICATIONS, 2016, 52 (37) : 6312 - 6315
  • [39] Controlled Delivery of H2O2: A Three-Enzyme Cascade Flow Reactor for Peroxidase-Catalyzed Reactions
    Arshi, Simin
    Madane, Ketan
    Shortall, Kim
    Hailo, Goran
    Alvarez-Malmagro, Julia
    Xiao, Xinxin
    Szymannska, Katarzyna
    Belochapkine, Serguei
    Ranade, Vivek V.
    Magner, Edmond
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2024, : 10555 - 10566
  • [40] Efficient Synthesis of Eight-Membered Nitrogen Heterocycles from O-Propargylic Oximes by Rhodium-Catalyzed Cascade Reactions
    Nakamura, Itaru
    Sato, Yoshinori
    Takeda, Keisuke
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (33) : 10214 - 10219