THE EFFICIENT SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN-2-(1H)-ONES AND THEIR SULFUR DERIVATIVES WITH H2SO4 IMMOBILIZED ON ACTIVATED CHARCOAL

被引:16
|
作者
Dilmaghani, Karim Akbari [1 ]
Zeynizadeh, Behzad [1 ]
Parasajam, Hadi [1 ]
机构
[1] Urmia Univ, Dept Chem, Fac Sci, Orumiyeh, Iran
关键词
3,4-Dihydropyrimidin-2(1H)-one; activated charcoal; H2SO4; Biginelli synthesis; ONE-POT SYNTHESIS; CATALYZED BIGINELLI REACTION; IMPROVED PROTOCOL CONDITIONS; CONDENSATION REACTION; CONVENIENT SYNTHESIS; RECYCLABLE CATALYST; SUPPORTED REAGENTS; REUSABLE CATALYST; ACID CATALYSIS; DIHYDROPYRIMIDINONES;
D O I
10.1080/10426507.2011.631644
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Various 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) and their sulfur derivatives were efficiently synthesized by a one-pot cyclocondensation reaction of aromatic and aliphatic aldehydes, beta-dicarbonyl compounds and urea (or thiourea) in the presence of sulfuric acid immobilized on activated charcoal (133% w/w). The reactions were carried out in refluxing n-hexane-acetonitrile (2.5:0.5 mL) within 5-150 min to give 3,4-dihydropyrimidinones (or thiones) in high to excellent yields (81-97%).
引用
收藏
页码:544 / 553
页数:10
相关论文
共 50 条
  • [41] Ionic Liquid Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Microwave Irradiation
    Wang, Qin
    Pei, Wen
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2010, 32 (06): : 806 - 808
  • [42] Synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) by natural L-ascorbic acid
    Kodape, Manisha M.
    Gawhale, Nandkishor D.
    Awjare, Nikita V.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2015, 54 (05): : 671 - 675
  • [43] Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
    A. Shaabani
    A. Maleki
    Chemical Papers, 2007, 61 : 333 - 336
  • [44] BiVO4-NPs: an efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives
    Shirini, Farhad
    Lati, Monireh Pourghasemi
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (01) : 75 - 87
  • [45] Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions
    Keivanloo, Ali
    Mirzaee, Mahdi
    Bakherad, Mohammad
    Soozani, Atena
    CHINESE JOURNAL OF CATALYSIS, 2014, 35 (03) : 362 - 367
  • [46] Microwave Irradiation Assisted Selective Synthesis of 4,6-Diaryl-3,4-dihydropyrimidin-2(1H)-ones and Pyrimidin-2(1H)-ones
    An, Lin
    Zhang, Ling
    Zheng, Youguang
    Xue, Yunsheng
    Mou, Jie
    Liu, Ling
    Liu, Yi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1108 - 1111
  • [47] Conducting Polyaniline is an Efficient Catalyst for Synthesis of 3,4-dihydropyrimidin-2-(1H)-one Derivative Under Solvent-Free Conditions
    Chabukswar, Vasant V.
    Handore, Kalpana N.
    Bhavsar, Sanjay V.
    Horne, Amit S.
    Dallavalle, Sabrina
    Gaikwad, Vishwas
    Mohite, Kakasaheb C.
    JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, 2013, 50 (04): : 411 - 415
  • [48] Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using Molybdenum(V) Chloride as a Catalyst
    Chari, M. Adharvana
    Shoba, D.
    Parameswari, S.
    Ramesh, Banala
    Pal, R. R.
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (01) : 15 - 17
  • [49] Grindstone chemistry: a highly efficient and green method for synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by L-tyrosine as an organocatalyst: a combined experimental and DFT study
    Khaskel, Anamika
    Gogoi, Prasanta
    Barman, Pranjit
    Bandyopadhyay, Biman
    RSC ADVANCES, 2014, 4 (67) : 35559 - 35567
  • [50] Solvent-Free and Catalyst-Free Biginelli Reaction to Synthesize 4-Alkyl-3,4-dihydropyrimidin-2-(1H)-ones
    Guo, Yongbiao
    Tang, Hui
    Gao, Zhenhua
    Meng, Xiangyan
    Yu, Huilan
    Zhong, Hui
    Huang, Guilan
    Zou, Chuanpin
    CHEMISTRYSELECT, 2017, 2 (27): : 8253 - 8255