Copper-catalyzed synthesis of 2-aminobenzimidazoles from carbonimidoyl dichlorides and amines

被引:12
|
作者
Yu, Hui [1 ]
Liu, Qiong [1 ]
Li, Yuzhe [1 ]
Ni, Chongzhi [1 ]
机构
[1] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China
基金
美国国家科学基金会;
关键词
2-Aminobenzimidazole; Copper-catalyzed; O-Haloaryl carbonimidoyl dichloride; BIFUNCTIONAL ORGANOCATALYSTS; O-HALOANILINES; EFFICIENT; DERIVATIVES; GUANYLATION; GUANIDINES;
D O I
10.1016/j.tetlet.2012.07.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new protocol for the synthesis of a variety of 2-aminobenzimidazole derivatives has been developed. O-haloaryl carbonimidoyl dichloride reacted with anilines to generate an o-haloaryl guanidine intermediate, which underwent copper catalyzed ring closure to afford 2-aminobenzimidazole derivative in moderate yields (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5253 / 5256
页数:4
相关论文
共 50 条
  • [1] Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles
    Saha, Prasenjit
    Ramana, Tamminana
    Purkait, Nibadita
    Ali, Md Ashif
    Paul, Rajesh
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22): : 8719 - 8725
  • [2] A Protocol to 2-Aminobenzimidazoles via Copper-Catalyzed Cascade Addition and Cyclization of o-Haloanilines and Carbodiimides
    Wang, Fei
    Cai, Shangjun
    Liao, Qian
    Xi, Chanjuan
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09): : 3174 - 3180
  • [3] Copper-Catalyzed CNH2 Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
    Rao, Desaboini Nageswar
    Rasheed, Sk.
    Kumar, Karampoori Anil
    Reddy, Annem Siva
    Das, Parthasarathi
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2126 - 2133
  • [4] SYNTHESIS AND TRANSFORMATIONS OF 2-AMINOBENZIMIDAZOLES
    SIMONOV, AM
    ANISIMOVA, VA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1979, (07): : 867 - 887
  • [5] Novel Synthesis of 2-Aminobenzimidazoles from Isoselenocyanates
    Xie, Yuanyuan
    Zhang, Fan
    Li, Jianjun
    Shi, Xiangjun
    SYNLETT, 2010, (06) : 901 - 904
  • [6] Copper- and palladium-catalyzed intramolecular aryl guanidinylation: An efficient method for the synthesis of 2-aminobenzimidazoles
    Evindar, G
    Batey, RA
    ORGANIC LETTERS, 2003, 5 (02) : 133 - 136
  • [7] Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles
    Pollock, Julie A.
    Kim, Sung Hoon
    Katzenellenbogen, John A.
    TETRAHEDRON LETTERS, 2015, 56 (44) : 6097 - 6099
  • [8] Copper-Catalyzed Direct Synthesis of Benzamides from Alcohols and Amines
    Bantreil, Xavier
    Fleith, Clement
    Martinez, Jean
    Lamaty, Frederic
    CHEMCATCHEM, 2012, 4 (12) : 1922 - 1925
  • [9] Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums
    Feng, Yadong
    Li, Yudong
    Cheng, Guolin
    Wang, Lianhui
    Cui, Xiuling
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14): : 7099 - 7107
  • [10] Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)2
    Hu, Dongyan
    Li, Mengsun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (08) : 1926 - 1931