An Aldehyde-Azomethine Imine [3+2]-Cycloaddition: High-Yielding Regioselective Synthesis of Substituted N,N-Bicyclic Pyrazolidinones

被引:4
|
作者
Gujral, Jagjeet [1 ]
Reddy, T. Prabhakar [1 ]
Gorachand, B. [1 ]
Ramachary, Dhevalapally B. [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Catalysis Lab, Hyderabad 500046, India
来源
CHEMISTRYSELECT | 2018年 / 3卷 / 27期
关键词
acetaldehydes; azomethine imines; N; N-bicyclic pyrazolidinones; click reaction; 3+2]-cycloaddition; 1,3-DIPOLAR CYCLOADDITION REACTION; AZIDE-ALKYNE CYCLOADDITION; METAL-FREE SYNTHESIS; CLICK CHEMISTRY; DIRECT ACCESS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; AZIDOPHENYL ARYLSELENIDES; STEREOSELECTIVE-SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; REGIOSPECIFIC SYNTHESIS;
D O I
10.1002/slct.201801328
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enolate mediated aldehyde-azomethine imine [3+2] cycloaddition of various aldehydes with N,N-cyclic azomethine imines is reported under DBU or tBuOK-catalysis. High reaction rate, ease of operation, simple catalyst, easily accessible starting materials and a wide substrate scope with numerous applications make this reaction an ideal addition to the click chemistry.
引用
收藏
页码:7900 / 7905
页数:6
相关论文
共 50 条
  • [21] Dearomative (3+2) cycloaddition of 2-substituted 3,5-dinitropyridines and N-methyl azomethine ylide
    Maxim A. Bastrakov
    Alexey K. Fedorenko
    Alexey M. Starosotnikov
    Vadim V. Kachala
    Svyatoslav A. Shevelev
    Chemistry of Heterocyclic Compounds, 2019, 55 : 72 - 77
  • [22] Base catalyzed abnormal [3+2]-cycloaddition reaction of isatin N,N′-cyclic azomethine imine with malononitrile via C-3 umpolung of oxindole
    Moghaddam, Firouz Matloubi
    Aghamiri, Bagher
    Eslami, Mohammad
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1299
  • [23] Dearomative (3+2) cycloaddition of 2-substituted 3,5-dinitropyridines and N-methyl azomethine ylide
    Bastrakov, Maxim A.
    Fedorenko, Alexey K.
    Starosotnikov, Alexey M.
    Kachala, Vadim V.
    Shevelev, Svyatoslav A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (01) : 72 - 77
  • [24] A [3+2] cycloaddition/C-arylation of isatinN,N′-cyclic azomethine imine 1,3-dipole with arynes
    Jin, Qiaomei
    Zhang, Dongjian
    Zhang, Jian
    RSC ADVANCES, 2020, 10 (51) : 30620 - 30623
  • [25] [3+3] Cycloaddition of Azomethine Imine: Synthesis of Bi- or Tricyclic N-Heterocycle
    Das, Tapas
    Sau, Madan
    Daripa, Bishnu
    Karmakar, Dipanjan
    Chakraborty, Sayan
    CHEMISTRYSELECT, 2020, 5 (25): : 7605 - 7626
  • [26] An Enolate-Mediated Organocatalytic Azide-Ketone [3+2]-Cycloaddition Reaction: Regioselective High-Yielding Synthesis of Fully Decorated 1,2,3-Triazoles
    Shashank, Adluri B.
    Karthik, S.
    Madhavachary, R.
    Ramachary, Dhevalapally B.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) : 16877 - 16881
  • [27] Gold catalyzed [3+2] cycloaddition of N-allenyl amides with azomethine imines
    Zhou, Wen
    Li, Xiao-Xiao
    Li, Guo-Hua
    Wu, Yun
    Chen, Zili
    CHEMICAL COMMUNICATIONS, 2013, 49 (34) : 3552 - 3554
  • [28] Expedient Synthesis of C-3-Ferrocenoyl-N-methylpyrrolidines via [3+2]-Cycloaddition Reaction of Azomethine Ylides
    Sureshbabu, A. R.
    Dhamodharan, V.
    Raghunathan, R.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (16) : 2889 - 2894
  • [29] Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3+2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides
    Blanco-Lopez, Ester
    Foubelo, Francisco
    Retamosa, Maria de Gracia
    Sansano, Jose M.
    ORGANIC LETTERS, 2023, 25 (45) : 8051 - 8056
  • [30] Asymmetric [3+2] Cycloaddition of Methyleneindolinones with N,N′-Cyclic Azomethine Imines Catalyzed by a N,N′-Dioxide Mg(OTf)2 Complex
    Yin, Chengkai
    Lin, Lili
    Zhang, Dong
    Feng, Juhua
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9691 - 9699