Synthesis of 3,4-dihydropyrimidin-2(1H)-one viaRetro-Biginellireaction

被引:5
|
作者
Mondal, Sudipta [1 ]
Mondal, Mohabul A. [1 ]
机构
[1] Jadavpur Univ, Dept Chem, 188,Raja SC Mallick Rd, Kolkata 700032, India
关键词
DERIVATIVES; DESIGN;
D O I
10.1002/jhet.4124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrolytic behavior of 5-acetyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one under alkaline condition has been explored. Mechanistic details are established by LCMS and HPLC. Evidence suggested that the deacetylative benzylidenation proceeds through the retro-Biginelli reaction. The scope of the retro-Biginelli reaction has been explored by the synthesis of substituted DHPs.
引用
收藏
页码:4175 / 4180
页数:6
相关论文
共 50 条
  • [21] Microwave assisted solid phase catalyst-free Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidin-2(1H)-thione: A green approach, characterization and molecular crystal structures
    Maru, Minaxi S.
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2016, 641 : 53 - 62
  • [22] Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1H)ones (-thiones)
    A. M. Magerramov
    M. M. Kurbanova
    R. T. Abdinbekova
    I. A. Rzaeva
    V. M. Farzaliev
    M. A. Allakhverdiev
    Russian Journal of Applied Chemistry, 2006, 79 : 787 - 790
  • [23] Synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones under microwave irradiation
    Afzal, MP
    Jayshankara, VP
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 14 (03) : 261 - 262
  • [24] Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1H) ones (-thiones)
    Magerramov, A.M.
    Kurbanova, M.M.
    Abdinbekova, R.T.
    Rzaeva, I.A.
    Farzaliev, V.M.
    Allakhverdiev, M.A.
    Russian Journal of Applied Chemistry, 2006, 79 (05): : 787 - 790
  • [25] SYNTHESIS OF 4-ALKYNYL-SUBSTITUTED 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES
    Novokshonov, Vladimir V.
    Novokshonova, Irina A.
    Nguyen, Hien T. T.
    Medvedeva, Alevtina S.
    SYNTHETIC COMMUNICATIONS, 2012, 42 (16) : 2346 - 2354
  • [26] A suitable synthesis of 3,4-dihydropyrimidin-2(1H)ones/thiones by microwave irradiation
    Sha, MAP
    Shankara, VPJ
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (03) : 1858 - 1862
  • [27] Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1H)ones (-thiones)
    Magerramov, A. M.
    Kurbanova, M. M.
    Abdinbekova, R. T.
    Rzaeva, I. A.
    Farzaliev, V. M.
    Allakhverdiev, M. A.
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2006, 79 (05) : 787 - 790
  • [28] One Pot Biginelli Synthesis of Novel 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Sulfamic Acid
    Liu, Yuting
    Yang, Lan
    Liu, Bin
    Yin, Dawei
    Dang, Yang
    Yang, Xiaoming
    Zou, Qian
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (06) : 572 - 579
  • [29] Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
    Reddy, CV
    Mahesh, M
    Raju, PVK
    Babu, TR
    Reddy, VVN
    TETRAHEDRON LETTERS, 2002, 43 (14) : 2657 - 2659
  • [30] One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by nontoxic ionic liquid
    Li, M
    Guo, WS
    Wen, LR
    Zhang, XL
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (09) : 1062 - 1065