Sulfated polyborate: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via Biginelli reaction

被引:68
|
作者
Khatri, Chetan K. [1 ]
Rekunge, Deelip S. [1 ]
Chaturbhuj, Ganesh U. [1 ]
机构
[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Bombay, Maharashtra, India
关键词
SOLVENT-FREE CONDITIONS; BRONSTED ACID CATALYST; EFFICIENT SYNTHESIS; SULFUR DERIVATIVES; BORIC-ACID; RECYCLABLE CATALYST; HIGHLY EFFICIENT; SILICA-GEL; 3,4-DIHYDROPYRIMIDINONES; DIHYDROPYRIMIDINES;
D O I
10.1039/c6nj03120j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this report, an efficient high-yield method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via a three-component Biginelli reaction with various aldehydes, beta-ketoesters/beta-diketones and urea/thiourea is described. The reaction was catalyzed by sulfated polyborate under solvent free conditions at 100 degrees C. The catalyst was prepared and used as a Bronsted as welt as Lewis acid catalyst. The catalyst was prepared by dehydration of boric acid followed by sulfonation and was characterized by different analytical techniques. The key advantages of the present method are the ability to tolerate a variety of functional groups, high yields, short reaction times, solvent free conditions, easy work-up, and recyctability of the catalyst, thus providing economical as well as ecological advantages.
引用
收藏
页码:10412 / 10417
页数:6
相关论文
共 50 条
  • [1] Sulfonated Carbon Catalyzed Biginelli Reaction for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and -thiones
    Moghaddas, Maryam
    Davoodnia, Abolghasem
    Heravi, Majid M.
    Tavakoli-Hoseini, Niloofar
    CHINESE JOURNAL OF CATALYSIS, 2012, 33 (04) : 706 - 710
  • [2] Au Nanorod: An Efficient Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via the Multicomponent Biginelli Reaction
    Nhat-Hang Thi Nguyen
    Phuong-Phong Thi Nguyen
    Thuy-Duy Thi Nguyen
    Minh-Nguyet Thi Tran
    Thanh-Nguyen Thi Huynh
    Phuong Hoang Tran
    CHEMISTRYSELECT, 2017, 2 (13): : 3932 - 3936
  • [3] Phytic acid: a biogenic organocatalyst for one-pot Biginelli reactions to 3,4-dihydropyrimidin-2(1H)-ones/thiones
    Zhang, Qiguo
    Wang, Xin
    Li, Zhenjiang
    Wu, Wenzhuo
    Liu, Jingjing
    Wu, Hao
    Cui, Saide
    Guo, Kai
    RSC ADVANCES, 2014, 4 (38): : 19710 - 19715
  • [4] An efficient and recyclable L-proline triflate ionic liquid catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones via the multi-component Biginelli reaction
    Khan Manh Hua
    Phuong Hoang Tran
    Thach Ngoc Le
    ARKIVOC, 2019, : 406 - 415
  • [5] 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
  • [6] 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
  • [7] Three Component Reaction: An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Thiones Using Heterogeneous Catalyst
    Kamble, Vinod Tribhuvannathji
    Muley, Dnyanoba Baburao
    Atkore, Sandeep Tukaram
    Dakore, Sharad Digambarrao
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (03) : 388 - 392
  • [8] 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
  • [9] Synthesis of 3,4-dihydropyrimidin-2(1H)-one via one-pot Biginelli reaction under solvent-free conditions
    Peng, Huan
    Hu, Yulin
    Xing, Rong
    Fang, Dong
    MONATSHEFTE FUR CHEMIE, 2015, 146 (12): : 2053 - 2058
  • [10] Ammonium Dihydrogen Phosphate Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
    Tayebee, Reza
    Maleki, Behrooz
    Ghadamgahi, Malihe
    CHINESE JOURNAL OF CATALYSIS, 2012, 33 (04) : 659 - 665