Chemoselective reduction of aromatic nitro and azo compounds in ionic liquids using zinc and ammonium salts

被引：125
|
作者：
Khan, FA [1 ]
Dash, J [1 ]
Sudheer, C [1 ]
Gupta, RK [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 42期
关键词：
ionic liquids; zinc; reduction; nitroarenes; anilines; azo compounds; hydrazobenzenes;
D O I：
10.1016/j.tetlet.2003.08.080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nitroarenes were chemoselectively reduced to the corresponding amines using zinc and aqueous ammonium salts in ionic liquids as a safe and recyclable reaction medium. Our results specify the effect of ammonium salts in the process; the combination of Zn/NH4Cl in [bmim][PF6] or Zn/HCO2NH4 in [bmim][BF4] were the suitable conditions for the reduction of nitroarenes. Azobenzenes were also smoothly reduced to hydrazobenzenes with Zn/HCO2NH4 (aq.) in recyclable [bmim][BF4] without any over reduction to the corresponding anilines. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7783 / 7787
页数：5
相关论文
共 50 条
  • [1] Highly chemoselective reduction of aromatic nitro compounds by copper nanoparticles/ammonium formate
    Saha, Amit
    Ranu, Brindaban
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6867 - 6870
  • [2] Samarium-promoted Chemoselective Reduction of Aromatic Nitro Compounds in Ionic Liquid
    郑兴良
    张永敏
    Chinese Journal of Chemistry, 2002, (09) : 925 - 928
  • [3] Samarium-promoted chemoselective reduction of aromatic nitro compounds in ionic liquid
    Zheng, XL
    Zhang, YM
    CHINESE JOURNAL OF CHEMISTRY, 2002, 20 (09) : 925 - 928
  • [4] Lead-catalyzed synthesis of azo compounds by ammonium acetate reduction of aromatic nitro compounds
    Srinivasa, GR
    Abiraj, K
    Gowda, DC
    SYNTHETIC COMMUNICATIONS, 2003, 33 (24) : 4221 - 4227
  • [5] Ionic Liquid Immobilized Pd Nanocatalysts for Chemoselective Reduction of Aliphatic/Aromatic Nitro Compounds
    Prakash, Om
    Jangir, Bhawana
    Srivastava, Vivek
    LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (12) : 1170 - 1181
  • [6] Selective reduction of nitro groups in aromatic azo compounds
    Lauwiner, M
    Roth, R
    Rys, P
    Wissmann, J
    HETEROGENEOUS CATALYSIS AND FINE CHEMICALS IV, 1997, 108 : 231 - 238
  • [7] Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: reduction with hydriodic acid revisited
    Kumar, JSD
    Ho, MM
    Toyokuni, T
    TETRAHEDRON LETTERS, 2001, 42 (33) : 5601 - 5603
  • [8] Chemoselective Hydrogenation of Aromatic Nitro Compounds Using Diammonium Hydrogen Phosphite and Commercial Zinc Dust
    Kumar, K. Anil
    Shruthi, K. S.
    Naik, Nagaraja
    Gowda, D. Channe
    E-JOURNAL OF CHEMISTRY, 2008, 5 (04) : 914 - 917
  • [9] A novel strategy for the preparation of arylhydroxylamines: chemoselective reduction of aromatic nitro compounds using bakers' yeast
    Li, F
    Cui, JN
    Qian, XH
    Zhang, R
    CHEMICAL COMMUNICATIONS, 2004, (20) : 2338 - 2339
  • [10] Zinc-catalyzed ammonium formate reductions: Rapid and selective reduction of aliphatic and aromatic nitro compounds
    Gowda, DC
    Mahesh, B
    Gowda, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2001, 40 (01): : 75 - 77
12345