Amination of 5-Spiro-Substituted 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones

被引:3
|
作者
Khramtsova, Ekaterina E. [1 ]
Lystsova, Ekaterina A. [1 ]
Khokhlova, Evgeniya V. [1 ]
Dmitriev, Maksim V. [1 ]
Maslivets, Andrey N. [1 ]
机构
[1] Perm State Univ, Dept Chem, Ul Bukireva 15, Perm 614990, Russia
来源
MOLECULES | 2021年 / 26卷 / 23期
基金
俄罗斯科学基金会;
关键词
amination; carbodiimide; pyrrole-2-one; thermolysis; urea; INHIBITORS; DERIVATIVES; DISCOVERY;
D O I
10.3390/molecules26237179
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is a valuable scaffold in drug discovery. The replacement of the 3-oxy fragment in 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones-based compounds with a 3-amino one (3-amino analogs of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, 3-amino-1,5-dihydro-2H-pyrrol-2-ones) can play a crucial role in their biological effect. Thus, approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones are of significant interest. We developed an approach to 5-spiro-substituted 3-amino-1,5-dihydro-2H-pyrrol-2-ones that could not be obtained using previously reported approaches (reactions of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones with amines). The developed approach is based on the thermal decomposition of 1,3-disubstituted urea derivatives of 5-spiro-substituted 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, which were prepared via their reaction with carbodiimides.
引用
收藏
页数:16
相关论文
共 50 条
  • [41] Facile Domino Access to Unexpected Alkyl 3-Substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates
    Zhang, Ya-Ru
    Huang, Xiao
    Xu, Dong-Cheng
    Xie, Jian-Wu
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2013, 66 (08) : 959 - 962
  • [42] I2-DMSO-Mediated Cascade Cyclization of β-Ketosulfoxonium Ylides and β-Enaminones: Synthesis of Quaternary-Carbon-Centered 2-Hydroxy-pyrrol-3(2H)-ones
    Kumar Saini, Rahul
    Borpatra, Paran J.
    Kumar Pandey, Satyendra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [43] Asymmetric amination of 2-substituted indolin-3-ones catalyzed by natural cinchona alkaloids
    Guo, Jing
    Lin, Zi-Hui
    Chen, Kai-Bin
    Xie, Ying
    Chan, Albert S. C.
    Weng, Jiang
    Lu, Gui
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1400 - 1406
  • [44] Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction
    Marek, Lukas
    Kolman, Lukas
    Vana, Jiri
    Svoboda, Jan
    Hanusek, Jiri
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 527 - 539
  • [45] Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide
    Jebali, Khaoula
    Arfaoui, Aicha
    Saadi, Fatma
    Lebreton, Jacques
    Amri, Hassen
    SYNTHETIC COMMUNICATIONS, 2014, 44 (23) : 3400 - 3407
  • [46] Highly Efficient and Expedient Synthesis of 5-Hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-Catalyzed Tandem Intramolecular Enaminic Addition of Tertiary Enamides to Ketones and 1,3-Hydroxy Rearrangement
    Yang, Luo
    Lei, Chuan-Hu
    Wang, De-Xian
    Huang, Zhi-Tang
    Wang, Mei-Xiang
    ORGANIC LETTERS, 2010, 12 (17) : 3918 - 3921
  • [47] Synthesis of a-substituted 2-(1H-1,2,4-triazol-3-yl)acetates and 5-amino-2,4-dihydro-3H-pyrazol-3-ones via the Pinner strategy
    Khomenko, Dmytro M.
    Doroshchuk, Roman O.
    Ivanova, Hanna, V
    Zakharchenko, Borys, V
    Raspertova, Ilona, V
    Vaschenko, Oleksandr V.
    Shova, Sergiu
    Dobrydnev, Alexey, V
    Moroz, Yurii S.
    Grygorenko, Oleksandr O.
    Lampeka, Rostyslav D.
    TETRAHEDRON LETTERS, 2021, 69
  • [48] Copper-mediated Chan-Evans-Lam N-arylation of 5-methylene-4-aryl1,5-dihydro-2H-pyrrol-2-one derivatives
    Almohaywi, Basmah
    Iskander, George
    Yu, Tsz Tin
    Bhadbhade, Mohan
    Black, David St C.
    Kumar, Naresh
    TETRAHEDRON LETTERS, 2018, 59 (09) : 811 - 814
  • [49] Electrocatalytic cascade approach to the synthesis of dihydro-2′H,3H-spiro[1-benzofuran-2,5′-pyrimidines]
    Ryzhkov, Fedor V.
    Elinson, Michail N.
    Ryzhkova, Yuliya E.
    Vereshchagin, Anatoly N.
    Fakhrutdinov, Artem N.
    Egorov, Mikhail P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (06) : 672 - 678
  • [50] Synthesis of new derivatives of 5-(3,4-dihydro-2De-pyrrol-5-yl)-pyrimidine
    Gasparyan, S. P.
    Alexanyan, M. V.
    Arutyunyan, G. K.
    Kocharov, S. L.
    Martirosyan, A. H.
    Tamazyan, R. A.
    Ayvazyan, A. G.
    Panosyan, H. A.
    Danagulyan, G. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (11) : 1646 - 1653