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
  • [31] Synthesis and characterization of Pd(II) and Pt(II) complexes with triazolopyrimidine derivatives:: The crystal structure of [Pd2L2Cl4] where L=5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine
    Lekkas, Nikos
    Hadjiliadis, Nick
    Garoufis, Achilleas
    Kobe, Joseph
    Bernhardt, Paul V.
    Tiekink, Edward R. T.
    INORGANICA CHIMICA ACTA, 2006, 359 (13) : 4297 - 4303
  • [32] Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: Optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches
    Huang, Boshi
    Li, Cuicui
    Chen, Wenmin
    Liu, Tao
    Yu, Mingyan
    Fu, Lu
    Sun, Yueyue
    Liu, Huiqing
    De Clercq, Erik
    Pannecouque, Christophe
    Balzarini, Jan
    Zhan, Peng
    Liu, Xinyong
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 754 - 765
  • [33] Synthesis of 12-aryl-1-oxo-1,2,3,4,5,12-hexahydroindolo-[2,1-b]quinazoline-6-carbonitriles by recyclization of 11-aryl-1-oxo-2,3,4,5,10b,11-hexahydro-1H-indolo[2,3-b]quinoline-10b-carbonitriles
    B. V. Lichitsky
    D. V. Kozhinov
    L. G. Vorontsova
    Z. A. Starikova
    A. A. Dudinov
    M. M. Krayushkin
    Russian Chemical Bulletin, 2002, 51 : 1869 - 1874
  • [34] Synthesis of 12-aryl-1-oxo-1,2,3,4,5,12-hexahydroindolo[2,1-b]quinazoline-6-carbonitriles by recyclization of 11-aryl-1-oxo-2,3,4,5,10b,11-hexahydro-1H-indolo[2,3-b]quinoline-10b-carbonitriles
    Lichitsky, BV
    Kozhinov, DV
    Vorontsova, LG
    Starikova, ZA
    Dudinov, AA
    Krayushkin, MM
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (10) : 1869 - 1874
  • [35] Synthesis and regioselective N- and O-alkylation of 1H- or 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-azaxanthines) and transformation of their 3-alkyl derivatives into 1-alkyl isomers
    Islam, Rafiqul
    Nagamatsu, Tomohisa
    SYNTHESIS-STUTTGART, 2006, (24): : 4167 - 4179
  • [36] One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines
    Melekhina, Valeriya G.
    Komogortsev, Andrey N.
    Lichitsky, Boris, V
    Mityanov, Vitaly S.
    Fakhrutdinov, Artem N.
    Dudinov, Arkady A.
    Migulin, Vasily A.
    Nelyubina, Yulia, V
    Melnikova, Elizaveta K.
    Krayushkin, Michail M.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2840 - 2846
  • [37] The Mannich reaction in the synthesis of N,S-containing heterocycles 10. Recyclization of stable cyclic michael adducts, N-methylmorpholinium 6-R-6-hydroxy-1,4,5,6-tetrahydropyridine-2-thiolates, to pyrimido[4,3-b][1,3,5]thiadiazines under conditions of aminomethylation reaction
    V. V. Dotsenko
    K. A. Frolov
    S. G. Krivokolysko
    V. P. Litvinov
    Russian Chemical Bulletin, 2009, 58 : 1479 - 1483
  • [38] The Mannich reaction in the synthesis of N,S-containing heterocycles 10. Recyclization of stable cyclic michael adducts, N-methylmorpholinium 6-R-6-hydroxy-1,4,5,6-tetrahydropyridine-2-thiolates, to pyrimido[4,3-b][1,3,5]thiadiazines under conditions of aminomethylation reaction
    Dotsenko, V. V.
    Frolov, K. A.
    Krivokolysko, S. G.
    Litvinov, V. P.
    RUSSIAN CHEMICAL BULLETIN, 2009, 58 (07) : 1479 - 1483
1234