1,3,5-Tris(hydrogensulfato) Benzene: A New and Efficient Catalyst for Synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) Derivatives

被引:43
|
作者
Karimi-Jaberi, Zahed [1 ]
Pooladian, Baharak [1 ]
Moradi, Masoud [1 ]
Ghasemi, Ehsan [1 ]
机构
[1] Islamic Azad Univ, Firoozabad Branch, Dept Chem, Firoozabad, Fars, Iran
关键词
1,3,5-tris(hydrogensulfato) benzene; aromatic aldehydes; 1-phenyl-3-methylpyrazol-5-one; 4,4 '-(arylmethylene)bis(1H-pyrazol-5-ols); ethanol; multicomponent reaction; SOLID ACID CATALYST; SOLVENT-FREE CONDITIONS; SULFURIC-ACID; HETEROGENEOUS CATALYST; TRICHLOROACETIC-ACID; METAL-COMPLEXES; RAPID SYNTHESIS; AQUEOUS-MEDIA; PYRAZOLONES;
D O I
10.1016/S1872-2067(11)60477-4
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
1,3,5-Tris(hydrogensulfato) benzene (THSB) was easily prepared by the reaction between phloroglucinol and chlorosulfonic acid in dichloromethane at room temperature. This compound was then used as an efficient catalyst for the synthesis of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) through the condensation reactions of 1-phenyl-3-methylpyrazol-5-one with several different aromatic aldehydes in ethanol at 75 degrees C. The present methodology offers several advantages over existing methodologies, such as excellent yields, simple procedure, easy work-up and ecofriendly reaction conditions.
引用
收藏
页码:1945 / 1949
页数:5
相关论文
共 50 条
  • [41] Catalyst-free tandem Knoevenagel-Michael reaction of aldehydes and pyrazolin-5-one: fast and convenient approach to medicinally relevant 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s
    Elinson, Michail N.
    Sokolova, Olga O.
    Nasybullin, Ruslan F.
    HETEROCYCLIC COMMUNICATIONS, 2015, 21 (02) : 97 - 101
  • [42] Preparation of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s over 1,3-disulfonic acid imidazolium tetrachloroaluminate as a novel catalyst
    Khazaei, Ardeshir
    Zolfigol, Mohammad Ali
    Moosavi-Zare, Ahmad Reza
    Asgari, Zhila
    Shekouhy, Mohsen
    Zare, Abdolkarim
    Hasaninejad, Alireza
    RSC ADVANCES, 2012, 2 (21) : 8010 - 8013
  • [43] PEG-SO3H as a new, highly efficient and homogeneous polymeric catalyst for the synthesis of bis(indolyl)methanes and 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1Hpyrazol-5-ol)s in water
    A. Hasaninejad
    M. Shekouhy
    A. Zare
    S. M. S. Hoseini Ghattali
    N. Golzar
    Journal of the Iranian Chemical Society, 2011, 8 : 411 - 423
  • [44] Synthesis, structures and electrocatalytic properties of coordination polymers of 4,4′,4′′,4′′′-tetrakiscarboxyphenylsilane and 1,3,5-tris(2-methyl-1H-imidazol-1-yl)benzene
    Cao, Tingting
    Li, Yang
    Xie, Tinghui
    Wang, Xinfang
    Huang, Zuogang
    Yu, Huaguang
    CRYSTENGCOMM, 2024, 26 (07) : 985 - 994
  • [45] Synthesis of 4,4′-(arylmethylene)bis(3-carboxymethyl-1-phenyl-1H-pyrazol-5-ol)s using ionic liquid attached to colloidal silica nanoparticles in water
    Shahbazi-Alavi, Hossein
    Safaei-Ghomi, Javad
    Esmaili, Samane
    Nazemzadeh, Seyed Hadi
    JOURNAL OF CHEMICAL RESEARCH, 2017, (08) : 457 - 459
  • [46] Design, synthesis, antimicrobial evaluations and in silico studies of novel pyrazol-5(4H)-one and 1H-pyrazol-5-ol derivatives
    Pham, Em Canh
    Tuong Vi Le Thi
    Phan, Long Tieu
    Nguyen, Huong-Giang T.
    Le, Khanh N. B.
    Tuyen Ngoc Truong
    ARABIAN JOURNAL OF CHEMISTRY, 2022, 15 (03)
  • [47] Nanocrystalline Cu-ZnO as an Green Catalyst for One Pot Synthesis of 4,4′((phenyl)methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) Derivatives
    Shinde, Santosh
    Karale, Bhausaheb
    Bankar, Digambar
    Arbuj, Sudhir
    Moulavi, Mansur
    Annalnerkar, Dinesh
    Kim, Taesung
    Kanade, Kalurann
    JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2019, 19 (08) : 4623 - 4631
  • [48] An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media
    Gouda, Moustafa A.
    Abu-Hashem, Ameen A.
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2012, 5 (02) : 203 - 209
  • [49] A rapid, efficient, and high-yielding synthesis of 4,4'-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40)
    Vafaee, Asieh
    Davoodnia, Abolghasem
    Pordel, Mehdi
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (11) : 8343 - 8354
  • [50] A rapid, efficient, and high-yielding synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40)
    Asieh Vafaee
    Abolghasem Davoodnia
    Mehdi Pordel
    Research on Chemical Intermediates, 2015, 41 : 8343 - 8354