A facile one-pot synthesis of benzimidazoles from 2-nitroanilines by reductive cyclization

被引：0
|
作者：
Liu, Zheng [1 ]
Li, Haihong [2 ]
Zhao, Qingjie [1 ]
Shen, Jingshan [1 ,2 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[2] Topharman Shanghai Co Ltd, Shanghai 201209, Peoples R China
来源：
HETEROCYCLES | 2008年 / 75卷 / 08期
关键词：
one-pot synthesis; benzimidazole; 2-nitroaniline; orthoester; reductive cyclization;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile one-pot process to prepare benzimidazole derivatives is described. Reductive cyclization of a serial of 2-nitroanilines with orthoesters in the presence of Pd/C in methanol at room temperature, which is promoted by a catalytic amount of acetic acid, affords the corresponding benzimidazole derivatives in high yields.
引用
收藏
页码：1907 / 1911
页数：5
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] Iron-catalyzed one-pot synthesis of benzimidazoles from 2-nitroanilines and benzylic alcohols
    Li, Gang
    Wang, Jin
    Yuan, Baokun
    Zhang, Dongfeng
    Lin, Ziyun
    Li, Peng
    Huang, Haihong
    [J]. TETRAHEDRON LETTERS, 2013, 54 (50) : 6934 - 6936
  • [3] One-pot synthesis of benzimidazoles from o-nitroanilines under microwaves via a reductive cyclization
    Surpur, Mandar P.
    Singh, Pankajkumar R.
    Patil, Sachin B.
    Samant, Shriniwas D.
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1375 - 1379
  • [4] 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
  • [5] 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
  • [6] 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
  • [7] One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium
    Go, Ahra
    Lee, Geunsoo
    Kim, Jaeho
    Bae, Seolhee
    Lee, Byung Min
    Kim, Byeong Hyo
    [J]. TETRAHEDRON, 2015, 71 (08) : 1215 - 1226
  • [8] Selective one-pot N-monomethylation of 2-nitroanilines under PTC conditions
    Voskresensky, S
    Makosza, M
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3523 - 3526
  • [9] Indium-mediated one-pot benzimidazole synthesis from 2-nitroanilines or 1,2-dinitroarenes with orthoesters
    Kim, Jaeho
    Kim, Jihye
    Lee, Hyunseung
    Lee, Byung Min
    Kim, Byeong Hyo
    [J]. TETRAHEDRON, 2011, 67 (41) : 8027 - 8033
  • [10] A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization
    Yang, DL
    Fokas, D
    Li, JZ
    Yu, LB
    Baldino, CM
    [J]. SYNTHESIS-STUTTGART, 2005, (01): : 47 - 56
12345