Microwave-assisted [3+2] cycloadditions of azomethine ylides

被引:52
|
作者
Bashiardes, G [1 ]
Safir, I [1 ]
Mohamed, AS [1 ]
Barbot, F [1 ]
Laduranty, J [1 ]
机构
[1] Univ Poitiers, SFA UMR 6514, Dept Chim Methodol & Synth Biomol, F-86022 Poitiers, France
关键词
D O I
10.1021/ol0361195
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The microwave-assisted intramolecular [3 + 2] cycloaddition reaction of azomethine ylides to activated and nonactivated alkenes and alkynes is described. The procedure allows the synthesis of pyrrolidines and pyrrole products in good to excellent overall yields in short reaction times. It appears from parallel comparative studies that the microwave procedure favors the reaction times and overall purity of the crude reaction mixture. The reactions can also be performed in the absence of solvent.
引用
收藏
页码:4915 / 4918
页数:4
相关论文
共 50 条
  • [1] 3+2 Cycloadditions on azomethine ylides
    Backous, Jeffrey P.
    Jasperse, Craig P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 692 - 692
  • [2] INTRAMOLECULAR [3+2] CYCLOADDITIONS OF FUNCTIONALIZED AZOMETHINE YLIDES
    CONFALONE, PN
    EARL, RA
    TETRAHEDRON LETTERS, 1986, 27 (24) : 2695 - 2698
  • [3] Solvent-free thermal and microwave-assisted [3+2] cycloadditions between stabilized azomethine ylides and nitrostyrenes.: An experimental and theoretical study
    Arrieta, Ana
    Otaegui, Dorleta
    Zubia, Aizpea
    Cossio, Fernando P.
    Diaz-Ortiz, Angel
    de la Hoz, Antonio
    Herrero, M. Antonia
    Prieto, Pilar
    Foces-Foces, Concepcion
    Pizarro, Jose L.
    Arriortua, Maria I.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12): : 4313 - 4322
  • [4] A facile synthesis of novel dispiroheterocycles through solvent-free microwave-assisted [3+2] cycloaddition of azomethine ylides
    Jayashankaran, J
    Manian, RDRS
    Raghunathan, R
    TETRAHEDRON LETTERS, 2004, 45 (39) : 7303 - 7305
  • [5] Benzoazepine-Fused Isoindolines via Intramolecular (3+2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
    Wales, Steven M.
    Rivinoja, Daniel J.
    Gardiner, Michael G.
    Bird, Melissa J.
    Meyer, Adam G.
    Ryan, John H.
    Hyland, Christopher J. T.
    ORGANIC LETTERS, 2019, 21 (12) : 4703 - 4708
  • [6] Organocatalytic diastereoselective synthesis of spirooxindoles via [3+2] cycloadditions of azomethine ylides with α,β-unsaturated esters
    Penaska, Tibor
    Ormandyova, Kristina
    Meciarova, Maria
    Filo, Juraj
    Sebesta, Radovan
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (13) : 5506 - 5512
  • [7] [3+2]-Cycloadditions of Azomethine Imines and Ynolates
    Winterton, Sarah E.
    Ready, Joseph M.
    ORGANIC LETTERS, 2016, 18 (11) : 2608 - 2611
  • [8] Enantio- and diastereoselective [3+2] cycloadditions of azomethine ylides with Ag(I)-phosphinooxazoline catalysts
    Stohler, R
    Wahl, F
    Pfaltz, A
    SYNTHESIS-STUTTGART, 2005, (09): : 1431 - 1436
  • [9] Catalyst-Controlled Chemodivergent [3+3] and [3+2] Formal Cycloadditions of Azomethine Ylides with Diphenylcyclopropenone
    Corpas, Javier
    Ponce, Alberto
    Maclean, Ian
    Adrio, Javier
    Carretero, Juan C.
    SYNTHESIS-STUTTGART, 2022, 54 (21): : 4673 - 4682
  • [10] Enantioselective dearomative [3+2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters
    Gerten, Anthony L.
    Stanley, Levi M.
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 339 - 343