Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Bronsted acidic ionic liquid

被引：26
|
作者：
Gajare, Shivanand [1 ]
Patil, Audumbar [1 ]
Hangirgekar, Shankar [1 ]
Dhanmane, Sushilkumar [2 ]
Rashinkar, Gajanan [1 ]
机构：
[1] Shivaji Univ, Dept Chem, Kolhapur 416004, MS, India
[2] Fergusson Coll, Dept Chem, Pune 411004, MS, India
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2020年 / 46卷 / 05期
关键词：
Bronsted acidic ionic liquid; Graphene oxide; A(3)-coupling; 2,4-disubstituted quinolines; Reusability; ONE-POT SYNTHESIS; 2,4-DISUBSTITUTED QUINOLINES; NANOCOMPOSITE; PERFORMANCE; CATALYSIS; ALDEHYDES; ALKYNES; AMINES;
D O I：
10.1007/s11164-020-04099-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS C-13 NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer-Emmett-Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A(3)-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product. Graphic abstract
引用
收藏
页码：2417 / 2436
页数：20
相关论文
共 50 条
  • [1] Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Brønsted acidic ionic liquid
    Shivanand Gajare
    Audumbar Patil
    Shankar Hangirgekar
    Sushilkumar Dhanmane
    Gajanan Rashinkar
    Research on Chemical Intermediates, 2020, 46 : 2417 - 2436
  • [2] Magnetic CuO nanoparticles supported on graphene oxide as an efficient catalyst for A3-coupling synthesis of propargylamines
    Mirabedini, Maryam
    Motamedi, Elaheh
    Kassaee, Mohammad Zaman
    CHINESE CHEMICAL LETTERS, 2015, 26 (09) : 1085 - 1090
  • [3] A GREEN, SOLVENT-FREE ONE-POT SYNTHESIS OF DISUBSTITUTED QUINOLINES VIA A3-COUPLING USING 1 MOL% FeCl3
    Naidoo, Shivani
    Jeena, Vineet
    HETEROCYCLES, 2016, 92 (09) : 1655 - 1664
  • [4] An expeditious synthesis of homoallylic alcohols using Bronsted acidic supported ionic liquid phase catalyst with pendant ferrocenyl group
    Rashinkar, Gajanan
    Kamble, Santosh
    Kumbhar, Arjun
    Salunkhe, Rajashri
    CATALYSIS COMMUNICATIONS, 2011, 12 (15) : 1442 - 1447
  • [5] A Modified and Green Procedure for the Synthesis of β-Amido Ketones Using a Bronsted-Acidic Ionic Liquid as Novel and Reusable Catalyst
    Davoodnia, Abolghasem
    Heravi, Majid M.
    Rezaei-Daghigh, Leila
    Tavakoli-Hoseini, Niloofar
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (03) : 429 - 433
  • [6] Synthesis of biodiesel via transesterification of tung oil catalyzed by new Bronsted acidic ionic liquid
    Yang, Jinbei
    Feng, Yaoyao
    Zeng, Ting
    Guo, Xiaoting
    Li, Ling
    Hong, Ruoyu
    Qiu, Ting
    CHEMICAL ENGINEERING RESEARCH & DESIGN, 2017, 117 : 584 - 592
  • [7] Nanoparticle Supported Bronsted Acidic Ionic Liquid Catalyzed Synthesis of Dihydro-1H-pyrazolylnaphthalene-1,4-diones
    Chandane, Wilson
    Gajare, Shivanand
    Patil, Audumbar
    Rashinkar, Gajanan
    Tamhankar, Bhaskar
    CATALYSIS LETTERS, 2023, 153 (11) : 3357 - 3370
  • [8] Ionic liquid assisted silver-catalyzed one-pot A3-coupling reactions for the synthesis of propargylamines
    Zhu, Anlian
    Du, Chunyan
    Zhang, Yue
    Li, Lingjun
    JOURNAL OF MOLECULAR LIQUIDS, 2019, 279 : 289 - 293
  • [9] Preparation and characterization of a dual acidic Ionic Liquid functionalized Graphene Oxide nanosheets as a Heterogeneous Catalyst for the Synthesis of pyrimido[4,5-b] quinolines in water
    Saleh, Mohanad Yakdhan
    Sadeek, Ghufran Th.
    Saied, Shakir Mahmood
    IRANIAN JOURNAL OF CATALYSIS, 2023, 13 (04): : 499 - 516
  • [10] Ionic Liquid Supported on Magnetic Graphene Oxide as a Highly Efficient and Stable Catalyst for the Synthesis of Triazolopyrimidines
    Jahanbakhshi, Azar
    Farahi, Mahnaz
    Aghajani, Yeganeh
    ACTA CHIMICA SLOVENICA, 2022, 69 (04) : 837 - 847
12345