Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones

被引：0
|
作者：
Nikolay S. Zimnitskiy
Alexey Yu. Barkov
Igor B. Kutyashev
Vladislav Yu. Korotaev
Vyacheslav Ya. Sosnovskikh
机构：
[1] Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin,
来源：
Chemistry of Heterocyclic Compounds | 2021年 / 57卷
关键词：
azomethine ylides; (; )-1,5-diarylpent-4-ene-1,3-diones; L-phenylglycine; L-proline; spiro[acenaphthylenepyrroli(zi)din]-2-ones; L-thiaproline; 1,3-dipolar cycloaddition;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A regio- and stereoselective method for the synthesis of spiro[acenaphthylenepyrroli(zi)din]-2-ones containing a 1,3-diketone fragment in their structure in 57–93% yields was developed. The method is based on (3+2) cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and α-amino acids (L-(thia)proline, L-phenylglycine) to (E)-1,5-diarylpent-4-ene-1,3-diones in EtOH at 60–70°C for 4–8 h.
引用
收藏
页码：743 / 750
页数：7
相关论文
共 50 条
  • [21] [3+2]-cycloaddition of nonstabilized azomethine ylides, part 9: A general approach for the construction of X-azabicyclo[m.2.1]alkanes optically pure form by asymmetric 1,3-dipolar cycloaddition reactions
    Pandey, G
    Laha, JK
    Mohanakrishnan, AK
    TETRAHEDRON LETTERS, 1999, 40 (33) : 6065 - 6068
  • [22] Diastereo- and Enantioselective Synthesis of Chiral Pyrrolidine-Fused Spirooxindoles via Organocatalytic [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylides with Maleimides
    Zhao, Hong-Wu
    Yang, Zhao
    Meng, Wei
    Tian, Ting
    Li, Bo
    Song, Xiu-Qing
    Chen, Xiao-Qin
    Pang, Hai-Liang
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2492 - 2502
  • [23] Regio- and stereoselective synthesis of novel spiropyrrolidines through 1,3-dipolar cycloaddition reactions of azomethine ylides and 2-styrylquinazolin-4(3H)-ones
    Maurya, Ram Awatar
    Nayak, Ranjita
    Reddy, Chada Narsimha
    Kapure, Jeevak Sopanrao
    Nanubolu, Jagadeesh Babu
    Singarapu, Kiran Kumar
    Ajitha, M.
    Kamal, Ahmed
    RSC ADVANCES, 2014, 4 (61): : 32303 - 32311
  • [24] 1,3-CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES GENERATED FROM 2-(TERT-BUTYL)-3-METHYLIMIDAZOLIDIN-4-ONE
    PEYRONEL, JF
    GRISONI, S
    CARBONI, B
    COURGEON, T
    CARRIE, R
    TETRAHEDRON, 1994, 50 (01) : 189 - 198
  • [25] 1,3-Dipolar cycloaddition of (E)-4-(4-chlorophenyl)-2-oxobut-3-enic acid to 2-oxindole azomethine ylides
    Tetiana L. Pavlovska
    Victoria V. Lipson
    Svetlana V. Shishkina
    Vladimir I. Musatov
    Alexander V. Borisov
    Alexander V. Mazepa
    Chemistry of Heterocyclic Compounds, 2019, 55 : 679 - 683
  • [26] 1,3-Dipolar cycloaddition of (E)-4-(4-chlorophenyl)-2-oxobut-3-enic acid to 2-oxindole azomethine ylides
    Pavlovska, Tetiana L.
    Lipson, Victoria V.
    Shishkina, Svetlana V.
    Musatov, Vladimir I.
    Borisov, Alexander V.
    Mazepa, Alexander V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (07) : 679 - 683
  • [27] [3+2]- versus [4+2]-cycloaddition reactions of 3-methylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with N-substituted maleimides involving pyrrolidine-derived azomethine ylides
    Deryabina, TG
    Belskaia, NP
    Kodess, MI
    Dehaen, W
    Toppet, S
    Bakulev, VA
    TETRAHEDRON LETTERS, 2006, 47 (11) : 1853 - 1855
  • [28] Diversity-oriented synthesis of three skeletally diverse iminolactones from isocyanides, activated acetylenes and 1H-pyrrole-2,3-diones via [3+2] and [4+1] cycloaddition reactions
    Moroz, Anna A.
    Zhulanov, Vladimir E.
    Dmitriev, Maksim, V
    Maslivets, Andrey N.
    TETRAHEDRON, 2020, 76 (05)
  • [29] Azomethine Ylides Derived from Alkyl- (3-Oxopiperazin-2-yl)Acetates in 1,3-Dipolar Cycloaddition Reactions with n-Aryl Maleimides
    Medvedeva, S. M.
    Stashina, G. A.
    Firgang, S. I.
    Malikova, E. S.
    Krysin, M. Yu.
    Shikhaliev, Kh. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (04) : 537 - 543
  • [30] Azomethine Ylides Derived from Alkyl- (3-Oxopiperazin-2-yl)Acetates in 1,3-Dipolar Cycloaddition Reactions with n-Aryl Maleimides
    S. M. Medvedeva
    G. A. Stashina
    S. I. Firgang
    E. S. Malikova
    M. Yu. Krysin
    Kh. S. Shikhaliev
    Chemistry of Heterocyclic Compounds, 2014, 50 : 537 - 543
12345