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
  • [41] Synthesis of biscoumarin derivatives using poly(4-vinylpyridine)-supported dual acidic ionic liquid as a heterogeneous catalyst
    Boroujeni, Kaveh Parvanak
    Ghasemi, Parvin
    Rafienia, Zahra
    MONATSHEFTE FUR CHEMIE, 2014, 145 (06): : 1023 - 1026
  • [42] Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Bronsted Acidic Ionic Liquid
    Liu, Weihua
    Gao, Shutao
    Feng, Cheng
    Zang, Xiaohuan
    Zhou, Xin
    Ma, Jingjun
    Wang, Chun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (05) : 962 - 965
  • [43] Synthesis of biscoumarin derivatives using poly(4-vinylpyridine)-supported dual acidic ionic liquid as a heterogeneous catalyst
    Kaveh Parvanak Boroujeni
    Parvin Ghasemi
    Zahra Rafienia
    Monatshefte für Chemie - Chemical Monthly, 2014, 145 : 1023 - 1026
  • [44] Synthesis of Highly Substituted Imidazoles Using Bronsted Acidic Ionic Liquid, Triphenyl(propyl-3-sulphonyl)phosphonium Toluenesulfonate, as Reusable Catalyst
    Shaterian, H. R.
    Ranjbar, M.
    Azizi, K.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (04) : 1120 - 1134
  • [45] Green synthesis of monolithic column incorporated with graphene oxide using room temperature ionic liquid and eutectic solvents for capillary electrochromatography
    Li, Xin-Xin
    Zhang, Li-Shun
    Wang, Chao
    Huang, Yan-Ping
    Liu, Zhao-Sheng
    TALANTA, 2018, 178 : 763 - 771
  • [46] Bronsted acidic ionic liquid as the efficient and reusable catalyst for synthesis of coumarins via Pechmann condensation under solvent-free conditions
    Hajipour, Abdol R.
    Sheikhan, Nafisehsadat
    Alaei, M. Ali
    Zarei, Amin
    IRANIAN JOURNAL OF CATALYSIS, 2015, 5 (03): : 231 - 236
  • [47] Facile synthesis of graphene oxide-supported CoOx nanoparticles for efficient degradation of antibiotics via percarbonate activation: Performance, degradation pathway and mechanism
    Chen, Shaona
    Liang, Yanhua
    Li, Bo
    Yang, Shuping
    Sun, Shilin
    Yang, Zihan
    Meng, Xu
    Dai, Zhongxu
    Liu, Xiang
    COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2023, 675
  • [48] Graphene oxide supported dicationic ionic liquid: an efficient catalyst for the synthesis of 1-carbamatoalkyl-2-naphthols
    Nipun Patel
    Deepak Katheriya
    Harsh Dadhania
    Abhishek Dadhania
    Research on Chemical Intermediates, 2019, 45 : 5595 - 5607
  • [49] Synthesis of a novel multi-SO3H functionalized strong Bronsted acidic ionic liquid and its catalytic activities for acetalization
    Zhang Jing
    Bao ShaoHua
    Yang JianGuo
    CHINESE SCIENCE BULLETIN, 2009, 54 (21): : 3958 - 3964
  • [50] Efficient Synthesis of Pyrimido[1,2-a]Benzimidazoles and Ethyl Pyrimido[1,2-a]Benzimidazole-3-Carboxylates Using Bronsted Acidic Ionic Liquid Supported on Nanoporous Na+-Montmorillonite
    Makhsous, Masoumeh
    Shirini, Farhad
    Seddighi, Mohadeseh
    Mazloumi, Masoumeh
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (02) : 494 - 501
12345