Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

被引:29
|
作者
Gan, Zongjie [1 ,2 ]
Tian, Qingqiang [1 ,2 ]
Shang, Suqin [1 ,2 ]
Luo, Wen [1 ,2 ]
Dai, Zeshu [1 ,2 ]
Wang, Huajun [1 ,2 ]
Li, Dan [1 ,2 ]
Wang, Xuetong [1 ,2 ]
Yuan, Jianyong [1 ,2 ]
机构
[1] Chongqing Med Univ, Dept Med Chem, Coll Pharm, Chongqing 400016, Peoples R China
[2] Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Chongqing 400016, Peoples R China
关键词
Imidazolium chloride; Benzimidazoles; 2-Substituted benzimidazoles; Synthesis; CONVENIENT SYNTHESIS; BENZOTHIAZOLES; HETEROCYCLES; CYCLIZATION; SOLVENT; AMINES; ACIDS; CO2;
D O I
10.1016/j.tet.2018.11.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码:7450 / 7456
页数:7
相关论文
共 50 条
  • [1] Synthesis of benzimidazoles from o-phenylenediamines and DMF derivatives in the presence of PhSiH3
    Zhu, Jianhua
    Zhang, Zhenbei
    Miao, Chengxia
    Liu, Wei
    Sun, Wei
    TETRAHEDRON, 2017, 73 (25) : 3458 - 3462
  • [2] An Efficient Synthesis of 2-Substituted Benzimidazoles via Photocatalytic Condensation of o-Phenylenediamines and Aldehydes
    Kovvuri, Jeshma
    Nagaraju, Burri
    Kamal, Ahmed
    Srivastava, Ajay K.
    ACS COMBINATORIAL SCIENCE, 2016, 18 (10) : 644 - 650
  • [3] 2H-BENZIMIDAZOLES (ISOBENZIMIDAZOLES) .10. SYNTHESIS OF POLYSUBSTITUTED O-PHENYLENEDIAMINES AND THEIR CONVERSION INTO HETEROCYCLES, PARTICULARLY 2-SUBSTITUTED BENZIMIDAZOLES WITH KNOWN OR POTENTIAL ANTHELMINTIC ACTIVITY
    HAZELTON, JC
    IDDON, B
    SUSCHITZKY, H
    WOOLLEY, LH
    TETRAHEDRON, 1995, 51 (39) : 10771 - 10794
  • [4] Synthesis and antimicrobial screening of some acid chloride derivatives of 2-substituted benzimidazoles
    Gupta, Sandeep
    Pancholi, S. S.
    Gupta, M. K.
    ORIENTAL JOURNAL OF CHEMISTRY, 2009, 25 (01) : 219 - 222
  • [5] Cu-catalyzed convenient synthesis of 2-trifluoromethyl benzimidazoles via cyclization of o-phenylenediamines with hexafluoroacetylacetone
    Chen, Xia
    Zhou, Xiao-Yu
    Liu, Hai-Long
    Zhang, Sheng
    Bao, Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9542 - 9546
  • [6] Cyclization of o-phenylenediamines by CO2 in the presence of H2 for the synthesis of benzimidazoles
    Yu, Bo
    Zhang, Hongye
    Zhao, Yanfei
    Chen, Sha
    Xu, Jilei
    Huang, Changliang
    Liu, Zhimin
    GREEN CHEMISTRY, 2013, 15 (01) : 95 - 99
  • [7] Synthesis of 2-Substituted Benzimidazoles Catalyzed by Cyclic Phosphoric Acid
    Wang, Xiangbo
    Jian, Tengyue
    Ma, Xiaowei
    He, Lin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (11) : 2181 - 2186
  • [8] Synthesis of 1H-benzimidazoles via the condensation of o-phenylenediamines with DMF promoted by organic acid under microwave irradiation
    Li, Wenjuan
    Li, Xiao
    Hong, Hailong
    Xie, Ruijun
    Zhu, Ning
    SYNTHETIC COMMUNICATIONS, 2024, 54 (08) : 645 - 654
  • [9] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Nejati, Akbar
    GREEN CHEMISTRY, 2010, 12 (07) : 1237 - 1241
  • [10] Synthesis and biological activity of 2-substituted benzimidazoles
    Shetgiri, NP
    Kokitkar, SV
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 6 (03) : 207 - 210