A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation

被引:78
|
作者
Safari, Javad [1 ]
Zarnegar, Zohre [1 ]
机构
[1] Univ Kashan, Coll Chem, Dept Organ Chem, Lab Organ Compound Res, Kashan, Iran
关键词
Fe3O4; nanoparticles; Sulfamic acid; Imidazole; Solid acid catalyst; Ultrasound irradiation; ONE-POT SYNTHESIS; SILICA SULFURIC-ACID; TETRASUBSTITUTED IMIDAZOLES; TRISUBSTITUTED IMIDAZOLES; DERIVATIVES; FACILE; NANOPARTICLES;
D O I
10.1016/j.ultsonch.2012.10.004
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
Fe3O4 nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:740 / 746
页数:7
相关论文
共 50 条
  • [41] ZrO2-β-cyclodextrin catalyzed synthesis of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles under solvent free conditions and evaluation of their antibacterial study
    Girish, Yarabhally R.
    Kumar, Kothanahally S. Sharath
    Thimmaiah, Kuntebommanahalli N.
    Rangappa, Kanchugarakoppal S.
    Shashikanth, Sheena
    RSC ADVANCES, 2015, 5 (92) : 75533 - 75546
  • [42] Bronsted acidic ionic liquid catalyzed an eco-friendly and efficient procedure for synthesis of 2,4,5-trisubstituted imidazole derivatives under ultrasound irradiation and optimal conditions
    Hilal, D. A.
    Hanoon, H. D.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (02) : 1521 - 1538
  • [43] Tungstate Sulfuric Acid (TSA): A Green and Highly Efficient Catalyst for Novel and Known Polysubstituted Imidazoles Synthesis
    Karami, Bahador
    Eskandari, Khalil
    Azizi, Mahboobeh
    LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (10) : 722 - 732
  • [44] TMSOTf-Catalysed Synthesis of 2,4,5-Trisubstituted Imidazoles from Vinyl Azides and Nitriles
    Harisha, Mysore Bhyrappa
    Dhanalakshmi, Pandi
    Suresh, Rajendran
    Kumar, Raju Ranjith
    Muthusubramanian, Shanmugam
    Bhuvanesh, Nattamai
    CHEMISTRYSELECT, 2019, 4 (10): : 2954 - 2958
  • [45] One-Step Synthesis of 2,4,5-Trisubstituted Pyrimidines
    Zhang, Chuang-Jun
    Han, Wen-Yong
    Gao, Mi-Xiang
    Xu, Fei-Fei
    Zhang, Zun-Ting
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (05) : 1073 - 1078
  • [46] Chitosan-functionalized nano-titanium dioxide: a novel and highly efficient nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions
    Ghasemi, Mahdieh
    Amoozadeh, Ali
    Kowsari, Elaheh
    REACTION KINETICS MECHANISMS AND CATALYSIS, 2017, 120 (02) : 605 - 617
  • [47] Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles
    Chary, Mahankhali Venu
    Keerthysri, Nallani Chakravarthula
    Vupallapati, Srinivasu V. N.
    Lingaiah, N.
    Kantevari, Srinivas
    CATALYSIS COMMUNICATIONS, 2008, 9 (10) : 2013 - 2017
  • [48] Microwave-Assisted Nickel-Catalyzed One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles
    Chundawat, Tejpal Singh
    Sharma, Nutan
    Kumari, Poonam
    Bhagat, Sunita
    SYNLETT, 2016, 27 (03) : 404 - 408
  • [49] Three-Component, One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Catalyzed by TiCl4-SiO2 Under Conventional Heating Conditions or Microwave Irradiation
    Safari, Javad
    Khalili, Shiva Dehghan
    Banitaba, Sayed Hossein
    SYNTHETIC COMMUNICATIONS, 2011, 41 (16) : 2359 - 2373
  • [50] One-pot synthesis of 2,4,5-trisubstituted imidazoles catalyzed by dicationic magnetic room temperature ionic liquid
    Godajdar, Bijan Mombani
    Kiasat, Ali Reza
    IRANIAN JOURNAL OF CATALYSIS, 2013, 3 (04): : 229 - 235