Acid-Catalyzed [3+2] Cycloaddition of Enones with Azomethine Imines for Easy Access to Tetrahydropyrazolopyrazolones

被引:9
|
作者
Jovanovic, Jovana P. [1 ]
Bogdanovic, Goran A. [2 ]
Damljanovic, Ivan [1 ]
机构
[1] Univ Kragujevac, Fac Sci, Radoja Domanovica 12, Kragujevac 34000, Serbia
[2] Univ Belgrade, Vinca Inst Nucl Sci, POB 522, Belgrade 11001, Serbia
关键词
dipolar cycloaddition; N; N '-cyclic azomethine imine; enone; N '-bicyclic heterocycles; Lewis acid; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; FACILE ACCESS; HETEROCYCLES; PYRAZOLIDINONES; ANNULATION; ALLENOATES; COMPLEXES; YLIDES; ESTERS; AMIDES;
D O I
10.1055/s-0036-1588678
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aluminum chloride (AlCl3) or zirconium chloride (ZrCl4) catalyzes efficiently the [3+2] cycloaddition of N, N'-cyclic azomethine imines with enones which contain the vinyl group. The scope of the reaction towards various azomethine imines and enones has been explored. Access to diastereomerically pure 6-acyl-5-aryltetrahydropyrazolo[1,2-a] pyrazol-1(5H)-ones is provided by easy chromatographic separations.
引用
收藏
页码:664 / 668
页数:5
相关论文
共 50 条
  • [31] Chiral Bis(Imidazolidine) Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates
    Arai, Takayoshi
    Ogino, Yuta
    MOLECULES, 2012, 17 (05): : 6170 - 6178
  • [32] CuI-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Cyclobutenones
    Corpas, Javier
    Ponce, Alberto
    Adrio, Javier
    Carretero, Juan C.
    ORGANIC LETTERS, 2018, 20 (11) : 3179 - 3182
  • [33] Enantioselective ag(i)-catalyzed [3+2] cycloaddition of azomethine ylides.
    Zhang, XM
    Raghunath, M
    Longmire, J
    Wang, B
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U208 - U208
  • [34] Bronsted Acid or Lewis Acid Catalyzed [3+3] Cycloaddition of Azomethine Imines with N-Benzyl Azomethine Ylide: A Facile Access to Bicyclic N-Heterocycles
    Li, Shuo-ning
    Yu, Bin
    Liu, Jia
    Li, Hong-lian
    Na, Risong
    SYNLETT, 2016, 27 (02) : 282 - 286
  • [35] Bifunctional AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Zeng, W
    Zhou, YG
    ORGANIC LETTERS, 2005, 7 (22) : 5055 - 5058
  • [36] A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES
    BERGSTRASSER, U
    HOFFMANN, A
    REGITZ, M
    TETRAHEDRON LETTERS, 1992, 33 (08) : 1049 - 1052
  • [37] The Lewis acid-catalyzed [3+1+1] cycloaddition of azomethine ylides with isocyanides
    Soeta, Takahiro
    Miyamoto, Yoshiaki
    Fujinami, Shuhei
    Ukaji, Yutaka
    TETRAHEDRON, 2014, 70 (37) : 6623 - 6629
  • [38] Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N- Cyclic Azomethine Imines
    Liu, Xinyu
    Liu, Zhixin
    Hu, Yongyi
    Huang, Kuo-Wei
    Ajitha, Manjaly J.
    Wang, De
    ORGANIC LETTERS, 2023, 25 (18) : 3249 - 3253
  • [39] Thermal [3+2] cycloaddition reaction of azomethine imines with allenoates for dinitrogen-fused heterocycles
    Na, Risong
    Liu, Honglei
    Li, Zhen
    Wang, Bo
    Liu, Jun
    Wang, Ming-An
    Wang, Min
    Zhong, Jiangchun
    Guo, Hongchao
    TETRAHEDRON, 2012, 68 (10) : 2349 - 2356
  • [40] A highly efficient [3+2] cycloaddition of nitrile oxides and azomethine imines to N-vinylpyrroles
    Efremova, Mariia M.
    Molchanov, Alexander P.
    Stepakov, Alexander V.
    Kostikov, Rafael R.
    Shcherbakova, Victoriya S.
    Ivanov, Andrey V.
    TETRAHEDRON, 2015, 71 (14) : 2071 - 2078