Boehmite Silylpropyl Amine Sulfamic Acid as an Efficient and Recyclable Catalyst for the Synthesis of some Pyrazole Derivatives

被引:6
|
作者
Doosti, Rahele [1 ]
Bakherad, Mohammad [1 ]
Mirzaee, Mahdi [1 ]
Jadidi, Khosrow [2 ]
机构
[1] Shahrood Univ Technol, Sch Chem, Shahrood 3619995161, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran
关键词
Boehmite nanoparticle; reusable catalyst; sulfamic acid; pyrazoles; NANOPARTICLE-SUPPORTED MOLYBDENUM; MULTICOMPONENT SYNTHESIS; AQUEOUS-MEDIA; IONIC LIQUID; ONE-POT; EPOXIDATION; COMPLEXES; VANADIUM; ALKENES;
D O I
10.2174/1570178614666170505113009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Background: The design of biologically-active compounds is a challenging viewpoint in medicinal chemistry, and pyrazoles play a crucial role as biologically-active molecules. Methods: Up to now, a few examples have been reported for the synthesis of pyrazoles catalyzed by heterogeneous catalysts. In this work, a new boehmite silylpropyl amine sulfamic (m-SABNPs) was applied as a catalyst for one-pot synthesis of pyrazole derivatives. Results: It was found that this heterogeneous sulfamic acid is a highly efficient catalyst for the syntheses of 5-amino-1,3-aryl-1H-pyrazole-4-carbonitriles and pyrazolopyranopyrimidines in good to excellent yields and can be recovered by a simple filtration of the reaction solution and reused for five consecutive runs without significant loss of catalytic activity. Moreover, its structure was characterized by FT-IR spectroscopy, TGA, XRD, TEM and SEM techniques. Conclusion: An efficient, and convenient method was proposed for the synthesis of pyrazole derivatives catalyzed by heterogeneous sulfamic acid in high-to-excellent yields. This method offers several advantages like milder reaction condition, shorter reaction time, cleaner reaction, and reusability of the catalyst.
引用
收藏
页码:450 / 460
页数:11
相关论文
共 50 条
  • [31] Synthesis of thiazole derivatives using magnetic nano zirconia–sulfuric acid as an efficient and recyclable catalyst in water
    A. Nakhaei
    Russian Journal of General Chemistry, 2017, 87 : 1850 - 1856
  • [32] Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
    Rahi, Tahere
    Baghernejad, Mojtaba
    Niknam, Khodabakhsh
    CHINESE JOURNAL OF CATALYSIS, 2012, 33 (07) : 1095 - 1100
  • [33] Silica-bonded N-propyl diethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of α-aminonitriles
    Rahi, Tahere
    Baghernejad, Mojtaba
    Niknam, Khodabakhsh
    Chinese Journal of Catalysis, 2012, 33 (7-8): : 1095 - 1100
  • [34] Synthesis of thiazole derivatives using magnetic nano zirconia-sulfuric acid as an efficient and recyclable catalyst in water
    Nakhaei, A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (08) : 1850 - 1856
  • [35] Silica bonded N-(propylcarbamoyl)sulfamic acid (SBPCSA) as a highly efficient and recyclable solid catalyst for the synthesis of Benzylidene Acrylate derivatives: Docking and reverse docking integrated approach of network pharmacology
    Aslam, Afroz
    Parveen, Mehtab
    Alam, Mahboob
    Silva, Manuela Ramos
    Pereira Silva, P. S.
    BIOPHYSICAL CHEMISTRY, 2020, 266
  • [36] Sulfamic acid:: An efficient and cost-effective solid acid catalyst for the synthesis of α-aminophosphonates at ambient temperature
    Mitragotri, S. D.
    Pore, D. M.
    Desai, U. V.
    Wadgaonkar, P. P.
    CATALYSIS COMMUNICATIONS, 2008, 9 (09) : 1822 - 1826
  • [37] Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives
    Luo, Haitang
    Kang, Yuru
    Li, Qi
    Yang, Liming
    HETEROATOM CHEMISTRY, 2008, 19 (02) : 144 - 148
  • [38] Sulfamic acid as an efficient and recyclable catalyst for the ring opening of epoxides with amines and anilines:: An easy synthesis of β-amino alcohols under solvent-free conditions
    Kamal, Ahmed
    Prasad, B. Rajendra
    Reddy, A. Malla
    Khan, M. Naseer A.
    CATALYSIS COMMUNICATIONS, 2007, 8 (12) : 1876 - 1880
  • [39] Sulfamic Acid: A Mild, Efficient, and Cost-Effective Catalyst for Synthesis of Indoloquinoxalines at Ambient Temperature
    Hegade, Pravin G.
    Mane, Mansing M.
    Patil, Jayavant D.
    Pore, Dattaprasad M.
    SYNTHETIC COMMUNICATIONS, 2014, 44 (23) : 3384 - 3391
  • [40] SULFAMIC ACID: EFFICIENT, COST-EFFECTIVE CATALYST FOR FACILE SYNTHESIS OF DEAZAOXAFLAVIN AT AMBIENT TEMPERATURE
    Mane, Mansing M.
    Pore, Dattaprasad M.
    SYNTHETIC COMMUNICATIONS, 2015, 45 (07) : 868 - 876