An efficient three-component one-pot synthesis of 3, 4-dihydropyrimidin-2-(1H)-thione derivatives with a mesoporous iron ion exchanged Indian clay catalyst

被引:0
|
作者
Kancherla, Mahesh [1 ,3 ]
Seku, Kondaiah [2 ]
Badathala, Vijayakumar [3 ]
机构
[1] Govt India, Reg Res Inst Unani Med NABH & NABL Accredited CCRU, Drug Standardizat Res Unit, Minist AYUSH, Chennai 600013, India
[2] Univ Technol & Appl Sci, Coll Engn & Technol, Engn Dept, POB 77, Shinas 324, Oman
[3] Vel Tech High Tech Dr Rangarajan Dr Sakunthala Eng, Dept Chem, Chennai 600062, India
关键词
Catalysis; Mesoporous clay catalyst; Fe3+-ExIC; Biginelli reaction; Dihydropyrimidine-2(1H)-thione; RAPID SYNTHESIS; BIGINELLI-TYPE; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; NANOPARTICLES; FACILE; THIONE; GREEN;
D O I
10.1007/s11164-024-05247-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This research work focuses on the potential usefulness of iron ion-exchanged Indian bentonite for one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-thiones. Our goal was to produce mesoporous Fe3+-exchanged Indian clay (Fe3+-ExIC) and its supported forms through a wet impregnation technique. The physicochemical properties of the catalysts, such as XRD, FTIR, TGA, physisorption studies, SEM, and acidity, were investigated. It was found that Fe3+-ExIC catalysts are efficient and reusable acidic heterogeneous catalysts for the synthesis of 3,4-dihydropyrimidine-2(1H)-thiones by refluxing aldehyde, methyl acetoacetate and thiourea with acetonitrile in cyclocondensation. An optimized reaction condition was found for preparing 5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione. A possible mechanism for the synthesis of 3,4-dihydropyrimidine-2(1H)-thiones has been proposed. Melting point, FTIR, and proton NMR were used to identify the products. Adequate catalyst activity was maintained over a period of six cycles, and a reduction in activity was attributed to a decrease in the acidity of the recycled catalyst.
引用
收藏
页码:2307 / 2324
页数:18
相关论文
共 50 条
  • [31] One-pot, multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives containing ferrocenyl
    Liu, Yuting
    Dang, Yang
    Yin, Dawei
    Yang, Xiaoming
    Yang, Lan
    Zou, Qian
    RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (01) : 547 - 555
  • [32] Organoclay as a Highly Efficient Catalyst for Three-Component One-Pot Biginelli Synthesis of Octahydroquinazolinone Derivatives
    Sayyahi, Soheil
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (11) : 6471 - 6472
  • [33] One-pot, multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives containing ferrocenyl
    Yuting Liu
    Yang Dang
    Dawei Yin
    Xiaoming Yang
    Lan Yang
    Qian Zou
    Research on Chemical Intermediates, 2020, 46 : 547 - 555
  • [34] Agar: a novel, efficient, and biodegradable catalyst for the one-pot three-component and green synthesis of 2,3-dihydroquinazolin-4(1H)-one, 4H-pyrimidobenzothiazole and 2-aminobenzothiazolomethylnaphthol derivatives
    Ashraf Moradi
    Reza Heydari
    Malek Taher Maghsoodlou
    Research on Chemical Intermediates, 2015, 41 : 7377 - 7391
  • [35] Agar: a novel, efficient, and biodegradable catalyst for the one-pot three-component and green synthesis of 2,3-dihydroquinazolin-4(1H)-one, 4H-pyrimidobenzothiazole and 2-aminobenzothiazolomethylnaphthol derivatives
    Moradi, Ashraf
    Heydari, Reza
    Maghsoodlou, Malek Taher
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (10) : 7377 - 7391
  • [36] Magnetic BiFeO3 nanoparticles: a robust and efficient nanocatalyst for the green one-pot three-component synthesis of highly substituted 3,4-dihydropyrimidine-2(1H)-one/thione derivatives
    Hanifi, Safa
    Dekamin, Mohammad G.
    Eslami, Mohammad
    SCIENTIFIC REPORTS, 2024, 14 (01):
  • [37] Indion 190 resin: A green and recyclable catalyst for facile and efficient one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-one
    Chaskar, Atul
    Jaffer, Farhat
    Langi, Bhushan
    Yewale, Sampat
    Bodkhe, Akalpita
    Journal of the Korean Chemical Society, 2009, 53 (02): : 224 - 228
  • [38] Indion 190 Resin: A Green and Recyclable Catalyst for Facile and Efficient One-pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-one
    Chaskar, Atul
    Jaffer, Farhat
    Langi, Bhushan
    Yewale, Sampat
    Bodkhe, Akalpita
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2009, 53 (02): : 224 - 228
  • [39] Titanium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1h)-ones under solvent-free conditions via three-component Biginelli reaction
    Valizadeh, H.
    Gholipur, H.
    Zarrebin, R.
    Amiri, M.
    Sabzi, M. R.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (07) : 1552 - 1555
  • [40] A one-pot multicomponent facile synthesis of dihydropyrimidin-2(1H)-thione derivatives using triphenylgermane as a catalyst and its binding pattern validation
    Andleeb, Sohaila
    Imtiaz-ud-Din
    Rauf, Muhammad Khawar
    Azam, Syed Sikander
    Badshah, Amin
    Sadaf, Haseeba
    Raheel, Ahmed
    Tahir, Muhammad Nawaz
    Raza, Saad
    RSC ADVANCES, 2016, 6 (83) : 79651 - 79661