Formal [3+2] cycloaddition of Ugi adducts towards pyrrolines

被引：13
|
作者：
Ben Abdessalem, Abdelbari [1 ]
Abderrahim, Raoudha [2 ]
Agrebie, Asma [1 ]
Dos Santos, Aurelie [1 ]
El Kaim, Laurent [1 ]
Komesky, Andrew [1 ]
机构：
[1] ENSTA ParisTech, Ecole Polytech, CNRS, ENSTA,Lab Chim & Proc,UMR 7652, F-91120 Palaiseau, France
[2] Univ Carthage, Fac Sci Bizerte, Lab Phys Lamellaires Mat & Hybrids Nanomat, Zarzouna 7021, Bizerte, Tunisia
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 06期
关键词：
ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS; AZOMETHINE YLIDES; MULTICOMPONENT REACTIONS; HETEROCYCLIC-COMPOUNDS; BOC/CYCLIZE STRATEGY; PROLINE DERIVATIVES; ALKALOIDS; CHEMISTRY; INDOLIZIDINE; CONSTRUCTION;
D O I：
10.1039/c4cc08282f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Ugi adducts derived from aromatic aldehydes may be converted to pyrrolines via addition of Michael acceptors under microwave irradiation. The reaction may proceed via unusual formation of azomethine ylides followed by a [3+2] cycloaddition using Michael acceptors.
引用
收藏
页码：1116 / 1119
页数：4
相关论文
共 50 条
  • [21] A new synthetic method for cyclopentanones via formal [3+2] cycloaddition reaction
    Domon, KMK
    Tanino, K
    Kuwajima, I
    SYNLETT, 1996, (02) : 157 - 158
  • [22] Catalytic Intramolecular Formal [3+2] Cycloaddition for the Synthesis of Benzobicyclo[4.3.0] Compounds
    Han, Xun
    Ye, Long-Wu
    Sun, Xiu-Li
    Tang, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3394 - 3397
  • [23] Au-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Isocyanoacetates with Maleimides
    Padilla, Silvia
    Adrio, Javier
    Carretero, Juan C.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08): : 4161 - 4166
  • [24] [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines
    Yuriy N. Markitanov
    Vadim M. Timoshenko
    Eduard B. Rusanov
    Yuriy G. Shermolovich
    Chemistry of Heterocyclic Compounds, 2021, 57 : 253 - 260
  • [25] Nucleophilic phosphine-catalyzed [3+2] cycloaddition of allenes with N-(thio)phosphoryl imines and acidic methanolysis of adducts N-(thio)phosphoryl 3-pyrrolines:: a facile synthesis of free amine 3-pyrrolines
    Zhang, Bo
    He, Zhengrong
    Xu, Silong
    Wu, Guiping
    He, Zhengjie
    TETRAHEDRON, 2008, 64 (40) : 9471 - 9479
  • [26] [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles - synthesis of pyrroles and pyrrolines
    Markitanov, Yuriy N.
    Timoshenko, Vadim M.
    Rusanov, Eduard B.
    Shermolovich, Yuriy G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (03) : 253 - 260
  • [27] Electrochemical formal [3+2] cycloaddition of azobenzenes with hexahydro-1,3,5-triazines
    Li, Chao
    Zhong, Qiang
    Tang, Shujun
    Wang, Lei
    Li, Pinhua
    Li, Hongji
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (14) : 3769 - 3774
  • [28] Asymmetric Formal [3+2] Cycloaddition Reactions of 3-Isothio-cyanato Oxindoles: an Update
    Tan, Fen
    He, Xiao-Yu
    Yang, Qing-Qing
    Zou, You-Quan
    SYNLETT, 2023, 34 (04) : 301 - 313
  • [29] Scope of the formal [3+2] cycloaddition for the synthesis of substituted 3-arylindanes and related compounds
    Lantano, Beatriz
    Aguirre, Jose Manuel
    Ugliarolo, Esteban Ariel
    Benegas, Maria Laura
    Moltrasio, Graciela Yolanda
    TETRAHEDRON, 2008, 64 (18) : 4090 - 4102
  • [30] Formal synthesis of Aspidosperma alkaloids via the intramolecular [3+2] cycloaddition of 2-azapentadienyllithiums
    Pearson, WH
    Aponick, A
    ORGANIC LETTERS, 2006, 8 (08) : 1661 - 1664
12345