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
  • [21] Cu2O-Catalyzed Ullmann-type C-N cross-coupling reaction of carbazole and aryl chlorides
    Zhu, Baiyao
    Xiong, Wenfang
    Tan, Xiaobin
    Wu, Wanqing
    Jiang, Huanfeng
    TETRAHEDRON LETTERS, 2022, 109
  • [22] Cu2O-Promoted cascade reaction of O-halobenzoate and enaminones for the synthesis of isoquinolinone derivatives
    Liang, Yang
    Wang, Rui
    TETRAHEDRON LETTERS, 2023, 114
  • [23] Unveiling mechanisms in Cu2O-catalyzed electroreduction of CO2 through theoretical resolution using periodic boundary and saturation cluster models
    Cui, Cheng-Xing
    Liu, Hang
    Wang, Juan-Juan
    Qu, Ling-Bo
    Chen, Xue-Bo
    APPLIED SURFACE SCIENCE, 2024, 657
  • [24] Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates
    Nakamura, Itaru
    Onuma, Toshiki
    Zhang, Dong
    Terada, Masahiro
    TETRAHEDRON LETTERS, 2014, 55 (06) : 1178 - 1182
  • [25] Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion
    Liu, Wenbo
    Tang, Peichen
    Zheng, Yi
    Ren, Yun-Lai
    Tian, Xinzhe
    An, Wankai
    Zheng, Xianfu
    Guo, Yinggang
    Shen, Zhenpeng
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (21) : 3509 - 3513
  • [26] Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles
    Saha, Prasenjit
    Ali, Md Ashif
    Ghosh, Pokhraj
    Punniyamurthy, Tharmalingam
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5692 - 5699
  • [27] Facile and Selective Synthesis of 2-Substituted Benzimidazoles Catalyzed by FeCl3/Al2O3
    Chen, Guo-Feng
    Dong, Xiao-Yun
    E-JOURNAL OF CHEMISTRY, 2012, 9 (01) : 289 - 293
  • [28] Cascade synthesis of azoquinazolinones by Cu(I)-catalyzed C-N coupling/C-H activation/C-N formation reactions under O2
    Chen, Dingben
    Chen, Qiufang
    Liu, Miaochang
    Dai, Shuangqun
    Huang, Ling
    Yang, Jianguo
    Bao, Weiliang
    TETRAHEDRON, 2013, 69 (31) : 6461 - 6467
  • [29] Synthesis of imidazolidin-2-ones via the cascade reactions of α-chloroaldoxime O-methanesulfonates
    Duangjan, Chanikan
    Rukachaisirikul, Vatcharin
    Kaeobamrung, Juthanat
    TETRAHEDRON LETTERS, 2020, 61 (38)
  • [30] Nickel-Catalyzed Mizoroki-Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles
    Chen, Xu
    Lin, Jin
    Wang, Biao
    Tian, Xu
    ORGANIC LETTERS, 2020, 22 (19) : 7704 - 7708