Efficient synthesis of (5-oxo-6,7-dihydro-4H-[1,2,4]triazolo-[1,5-a]pyrimidin-6-yl)acetanilides based on the recyclization of N-arylitaconimides with 3-amino[1,2,4]triazoles

被引：7
|
作者：
Kovygin, Yu A. [1 ]
Vandyshev, D. Yu [1 ]
Ledenyova, I., V [1 ]
Kosheleva, E. A. [1 ]
Polikarchuk, V. A. [1 ]
Kozaderov, O. A. [1 ]
Shikhaliev, Kh S. [1 ]
机构：
[1] Voronezh State Univ, 1 Univ Skaya Pl, Voronezh 394018, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2021年 / 70卷 / 03期
基金：
俄罗斯科学基金会;
关键词：
triazolopyrimidines; itaconimides; recyclization;
D O I：
10.1007/s11172-021-3118-2
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A convenient method for the synthesis of 2-(2-R-5-oxo-6,7-dihydro-4H-[1,2,4]triazolo-[1,5-a]pyrimidin-6-yl)acetanilides based on the regioselective domino reaction of N-arylitaconimides with substituted 3-aminotriazoles was proposed. Presumably, the reaction pathway includes the conjugated aza-addition of the endo-nucleophilic center of triazole to imide, followed by the recyclization of the intermediate to triazolo[1,5-a]pyrimidine.
引用
收藏
页码：520 / 526
页数：7
相关论文
共 38 条
  • [1] Efficient synthesis of (5-oxo-6,7-dihydro-4H-[1,2,4]triazolo-[1,5-a]pyrimidin-6-yl)acetanilides based on the recyclization of N-arylitaconimides with 3-amino[1,2,4]triazoles
    Yu. A. Kovygin
    D. Yu. Vandyshev
    I. V. Ledenyova
    E. A. Kosheleva
    V. A. Polikarchuk
    O. A. Kozaderov
    Kh. S. Shikhaliev
    Russian Chemical Bulletin, 2021, 70 : 520 - 526
  • [2] Recyclization of N-arylitaconimides with carboximidamides – a novel efficient method for the synthesis of 2-(2-amino-6-oxo- 1,4,5,6-tetrahydropyrimidin-5-yl)acetanilides
    Nikita M. Sotnikov
    Yurii А. Kovygin
    Dmitrii Yu. Vandyshev
    Irina V. Ledenyova
    Yevgeniya А. Kosheleva
    Oleg А. Kozadyorov
    Khidmet S. Shikhaliev
    Chemistry of Heterocyclic Compounds, 2021, 57 : 154 - 158
  • [3] Recyclization of N-arylitaconimides with carboximidamides - a novel efficient method for the synthesis of 2-(2-amino-6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)acetanilides
    Sotnikov, Nikita M.
    Kovygin, Yurii A.
    Vandyshev, Dmitrii Yu.
    Ledenyova, Irina V.
    Kosheleva, Yevgeniya A.
    Kozadyorov, Oleg A.
    Shikhaliev, Khidmet S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (02) : 154 - 158
  • [4] Metal complexes of [1,2,4]triazolo-[1,5-a]pyrimidine derivatives
    Salas, JM
    Romero, MA
    Sánchez, MP
    Quirós, M
    COORDINATION CHEMISTRY REVIEWS, 1999, 193-5 : 1119 - 1142
  • [5] 5-Oxo and 7-oxo derivatives of [1,2,4]triazolo-[1,5-a]pyrimidine:: characterization and theoretical study
    Abul Haj, M
    Salas, JM
    Quirós, M
    Molina, J
    Faure, R
    JOURNAL OF MOLECULAR STRUCTURE, 2000, 519 : 165 - 172
  • [6] 4,5,6,7-tetrahydro-5,7-dioxo-[1,2,4]triazolo-[1,5-a]pyrimidine: characterisation and theoretical study
    Orihuela, S
    Sanchez, MP
    Quiros, M
    Molina, J
    Faure, R
    JOURNAL OF MOLECULAR STRUCTURE, 1997, 415 (03) : 285 - 292
  • [7] Molecular Structure of 3-Amino[1,2,4]Triazolo-[4,3-A]Pyrimidin-5-One in Various Tautomeric Forms: Investigation by DFT and QTAIM Methods
    A. V. Astakhov
    V. M. Chernyshev
    Chemistry of Heterocyclic Compounds, 2014, 50 : 319 - 326
  • [8] Molecular Structure of 3-Amino[1,2,4]Triazolo-[4,3-A]Pyrimidin-5-One in Various Tautomeric Forms: Investigation by DFT and QTAIM Methods
    Astakhov, A. V.
    Chernyshev, V. M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (03) : 319 - 326
  • [9] Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones
    Andrade, Valquiria P.
    Mittersteiner, Mateus
    Bonacorso, Helio G.
    Frizzo, Clarissa P.
    Martins, Marcos A. P.
    Zanatta, Nilo
    SYNTHESIS-STUTTGART, 2019, 51 (11): : 2311 - 2317
  • [10] A Simple Access in One Step to Some New Substituted Pyrazolo- and [1,2,4]triazolo-[1,5-a]pyrimidines
    Balti, Monaem
    Dridi, Khaireddine
    El Efrit, Mohamed Lotfi
    LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (02) : 118 - 120
1234