Environmentally Friendly Preparation of 3,4-Dihydropyrimidin-2(1H)-thiones Catalyzed by Al(H2PO4)3

被引:11
|
作者
Shaterian, Hamid Reza [1 ]
Hosseinian, Asghar [1 ]
Ghashang, Majid [1 ]
机构
[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran
关键词
Al(H2PO4)(3); Biginelli reaction; 3,4-dihydropyrimidin-2(1H)-thione; heterogeneous catalyst; multicomponent reaction; ONE-POT SYNTHESIS; CALCIUM-CHANNEL BLOCKERS; ADRENOCEPTOR-SELECTIVE ANTAGONISTS; BIGINELLI REACTION; ACID-ESTERS; DIHYDROPYRIMIDINONES; EFFICIENT; CONDENSATION; PHOSPHATES; DESIGN;
D O I
10.1080/10426500802080576
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient, facile, simple, and green synthetic protocol for the Biginelli reaction has been developed for the preparation of 3,4-dihydropyrimidin-2(1H)-thione derivatives under thermal and microwave irradiation, solvent-free conditions, in the presence of aluminum hydrogen phosphate, Al(H2PO4)3, as an environmentally friendly heterogeneous recyclable catalyst, in high to excellent yields and short reaction time. In addition, the catalyst could be easily recovered from the reaction mixture by simple filtration and reused several times without any loss of activity.
引用
收藏
页码:126 / 134
页数:9
相关论文
共 50 条
  • [1] HClO4-Al2O3as a Prominent Catalyst in the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones under Environmentally Friendly Solvent Conditions
    Zanin, Lucas L.
    Porto, Andre L. M.
    CHEMISTRYSELECT, 2020, 5 (28): : 8604 - 8608
  • [2] Al(HSO4)3 and Al2O3-SO3H as Efficient Catalysts for Modified Preparation of 3,4-Dihydropyrimidin-2(1H)-ones/thiones
    Shaterian, Hamid Reza
    Hosseinian, Asghar
    Ghashang, Majid
    Khorami, Fahimeh
    Karimpoor, Neda
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (09) : 2333 - 2338
  • [3] Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction
    Starcevich, Jacob T.
    Laughlin, Thomas J.
    Mohan, Ram S.
    TETRAHEDRON LETTERS, 2013, 54 (08) : 983 - 985
  • [4] Cost-effective ionic liquid for environmentally friendly synthesis of 3,4-dihydropyrimidin-2 (1H)-ones
    Chavan, Sunil S.
    Sharma, Yogesh O.
    Degani, Mariam S.
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2009, 2 (03) : 175 - 179
  • [5] 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
  • [6] Nano isopolyoxomolybdate catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones under solvent-free conditions
    Nakhaei, A.
    Davoodnia, A.
    Yadegarian, S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (12) : 2870 - 2876
  • [7] An Efficient Synthesis of Multi-Substituted 3,4-Dihydropyrimidin-2(1H)-ones/thiones Under Solvent-Free Microwave Irradiation Using Alumina Sulfuric Acid
    Shaterian, Hamid Reza
    Hosseinian, Asghar
    Ghashang, Majid
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (01) : 197 - 205
  • [8] Evaluation of alcohols as substrates for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions
    Keciek, Aleksandra
    Paprocki, Daniel
    Koszelewski, Dominik
    Ostaszewski, Ryszard
    CATALYSIS COMMUNICATIONS, 2020, 135
  • [9] Synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by poly(ferric 2-acrylamido-2-methylpropanesulfonate)
    Zhao, Zhihao
    Dai, Hongguang
    Shi, Lan
    CHEMICAL PAPERS, 2021, 75 (02): : 583 - 590
  • [10] Sulfamic Acid Supported Magnetic Fe3O4 Nanoparticles Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/Thiones
    Toosi, Foad Shaghayeghi
    Maghsoodi, Ali
    Toosi, Faranak Shaghayeghi
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2016, 46 (02) : 168 - 170