Iron-catalyzed one-pot synthesis of benzimidazoles from 2-nitroanilines and benzylic alcohols

被引:46
|
作者
Li, Gang [1 ,2 ,3 ]
Wang, Jin [1 ,2 ,3 ]
Yuan, Baokun [1 ,2 ,3 ]
Zhang, Dongfeng [1 ,2 ,3 ]
Lin, Ziyun [1 ,2 ,3 ]
Li, Peng [1 ,2 ,3 ]
Huang, Haihong [1 ,2 ,3 ]
机构
[1] Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Inst Mat Med, Beijing Key Lab Act Subst Discovery & Druggabil E, Beijing 100050, Peoples R China
[3] Chinese Acad Med Sci, Beijing 100050, Peoples R China
关键词
Benzimidazole; Hydrogen transfer; Dppf; One-pot synthesis; ANTICANCER AGENTS; EFFICIENT; DERIVATIVES; BENZAZOLES; INHIBITORS;
D O I
10.1016/j.tetlet.2013.10.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The iron-catalyzed heterocyclizations from 2-nitroanilines and benzylic alcohols to form benzimidazoles using hydrogen transfer reaction were investigated in this study. In the presence of dppf in toluene at 150 degrees C, various benzimidazoles were obtained in moderate to good yields within 24 h. The reaction was proposed to proceed via a cascade of alcohol oxidation, nitro reduction, condensation, and dehydrogenation. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6934 / 6936
页数:3
相关论文
共 50 条
  • [1] A mild, one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines
    Hornberger, Keith R.
    Adjabeng, George M.
    Dickson, Hamilton D.
    Davis-Ward, Ronda G.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (30) : 5359 - 5361
  • [2] A facile one-pot synthesis of benzimidazoles from 2-nitroanilines by reductive cyclization
    Liu, Zheng
    Li, Haihong
    Zhao, Qingjie
    Shen, Jingshan
    [J]. HETEROCYCLES, 2008, 75 (08) : 1907 - 1911
  • [3] Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
    Putta, Ramachandra Reddy
    Chun, Simin
    Lee, Seok Beom
    Hong, Junhwa
    Oh, Dong-Chan
    Hong, Suckchang
    [J]. RSC ADVANCES, 2021, 11 (30) : 18225 - 18230
  • [4] Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
    Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul
    08826, Korea, Republic of
    不详
    08826, Korea, Republic of
    [J]. RSC Adv., 1600, 30 (18225-18230):
  • [5] Indium-mediated one-pot synthesis of benzoxazoles or benzimidazoles from 2-nitrophenols or 2-nitroanilines
    Kim, Byeong Hyo
    Kim, Jihye
    Lee, Hye-Jeong
    Lee, Byung Min
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [6] Convenient two-step one-pot synthesis of benzimidazoles using 2-nitroanilines and thiourea dioxide
    Pu, Shuai
    Liang, Qiuxiang
    Luo, Xi
    Luo, Juan
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2014, (02) : 118 - 120
  • [7] Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions
    VanVliet, DS
    Gillespie, P
    Scicinski, JJ
    [J]. TETRAHEDRON LETTERS, 2005, 46 (39) : 6741 - 6743
  • [8] A Versatile Iron-Catalyzed Protocol for the One-Pot Synthesis of Isoxazoles or Isoxazolines from the Same Propargylic Alcohols
    Debleds, Olivier
    Gayon, Eric
    Ostaszuk, Emilie
    Vrancken, Emmanuel
    Campagne, Jean-Marc
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (40) : 12207 - 12213
  • [9] Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols
    Wang, Huamin
    Cao, Xiangxiang
    Xiao, Fuhong
    Liu, Saiwen
    Deng, Guo-Jun
    [J]. ORGANIC LETTERS, 2013, 15 (18) : 4900 - 4903
  • [10] Au catalyzed synthesis of benzimidazoles from 2-nitroanilines and CO2/H2
    Hao, Leiduan
    Zhao, Yanfei
    Yu, Bo
    Zhang, Hongye
    Xu, Huanjun
    Liu, Zhimin
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 3039 - 3044