Benzoazepine-Fused Isoindolines via Intramolecular (3+2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

被引：14
作者：
Wales, Steven M. [1 ]
Rivinoja, Daniel J. [1 ]
Gardiner, Michael G. [2 ]
Bird, Melissa J. [1 ]
Meyer, Adam G. [3 ]
Ryan, John H. [3 ]
Hyland, Christopher J. T. [1 ]
机构：
[1] Univ Wollongong, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia
[2] Univ Tasmania, Sch Nat Sci Chem, Hobart, Tas 7001, Australia
[3] CSIRO Biomed Mfg, Ian Wark Lab, Bayview Ave, Clayton, Vic 3168, Australia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 12期
关键词：
1,3-DIPOLAR CYCLOADDITION; DIASTEREOSELECTIVE SYNTHESIS; FACILE DEAROMATIZATION; DECARBOXYLATIVE ROUTE; DERIVATIVES; SYSTEMS; BONDS;
D O I：
10.1021/acs.orglett.9b01580
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted alpha-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, alpha-mono-, and alpha,alpha-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
引用
收藏
页码：4703 / 4708
页数：6
相关论文
共 50 条
  • [1] 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
  • [2] An expedient synthesis of ferrocene grafted spirooxindolopyrrolizidines via [3+2]-cycloaddition of azomethine ylides
    Babu, A. R. Suresh
    Raghunathan, R.
    Baskaran, Sundari
    TETRAHEDRON, 2009, 65 (11) : 2239 - 2243
  • [3] Dearomative [3+2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
    Wang, Kai-Kai
    Xie, Yan-Xin
    Li, Yan-Li
    Chen, Rongxiang
    Wang, Zhan-Yong
    RSC ADVANCES, 2020, 10 (48) : 28720 - 28724
  • [4] Synthesis of Ferrocenyl Pyrrolizidines Through [3+2] Cycloaddition of Azomethine Ylides
    Zhang, Yu-Mei
    Liu, Peng
    Zhang, Hong-Li
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2013, 43 (03) : 340 - 342
  • [5] Organocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides
    Fernandez, Naiara
    Carrillo, Luisa
    Vicario, Jose L.
    Badia, Dolores
    Reyes, Efraim
    CHEMICAL COMMUNICATIONS, 2011, 47 (45) : 12313 - 12315
  • [6] [3+1]- and [3+2]-Cycloadditions of Azaoxyallyl Cations and Sulfur Ylides
    Li, Chao
    Jiang, Kun
    Ouyang, Qin
    Liu, Tian-Yu
    Chen, Ying-Chun
    ORGANIC LETTERS, 2016, 18 (11) : 2738 - 2741
  • [7] 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
  • [8] Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands
    Caleffi, Guilherme S.
    Larranaga, Olatz
    Ferrandiz-Saperas, Marcos
    Costa, Paulo R. R.
    Najera, Carmen
    de Cozar, Abel
    Cossio, Fernando P.
    Sansano, Jose M.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17) : 10593 - 10605
  • [9] Catalytic Enantioselective [3+2] Cycloaddition of N-Metalated Azomethine Ylides
    Kumar, Sundaravel Vivek
    Guiry, Patrick J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)
  • [10] Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines
    Pozgan, Franc
    Al Mamari, Hamad
    Groselj, Uros
    Svete, Jurij
    Stefane, Bogdan
    MOLECULES, 2018, 23 (01):
12345