The first example of the reactions of cyclopropenes with N-acyliminium cations generated from hydroxylactams

被引：12
|
作者：
Larina, Anna G. [1 ]
Nosova, Vlada E. [1 ]
Filatov, Alexander S. [1 ]
Molchanov, Alexander P. [1 ]
Starova, Galina L. [1 ]
Zolotarev, Andrey A. [1 ]
Boitsov, Vitaly M. [2 ,3 ]
Stepakov, Alexander V. [1 ,4 ]
机构：
[1] St Petersburg State Univ, Univ Emb 7-9, St Petersburg 199034, Russia
[2] St Petersburg Acad Univ, RAS, Nanotechnol Res & Educ Ctr, Khlopin Str 8-3, St Petersburg 194021, Russia
[3] Pavlov First St Petersburg State Med Univ, Lva Tolstogo Str 6-8, St Petersburg 197022, Russia
[4] Voeikov Main Geophys Observ, Ul Karbysheva 7, St Petersburg 194021, Russia
来源：
TETRAHEDRON | 2016年 / 72卷 / 33期
基金：
俄罗斯科学基金会;
关键词：
Cyclopropenes; Hydroxylactams; N-Acyliminium cation; Fused-ring systems; Indenes; Lewis acids; DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; CYCLIZATIONS; DERIVATIVES; CHEMISTRY; ISOXAZOLOPYRROLOISOQUINOLINES; TRANSFORMATIONS; REARRANGEMENT; CONFORMATION; FLUORESCENCE;
D O I：
10.1016/j.tet.2016.06.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first example of the reactions of cyclopropenes with N-acyliminium cations is described. 3-(1H-Inden-3-yl)isoindolin-1-ones and cyclopropa[c]isoindolo[2,1-a]quinolones were prepared by BF3 center dot OEt2 mediated reactions of cyclopropenes with the N-acyliminium cations, generated from 2-aryl(benzyl)-3-hydroxyisoindolin-1-ones. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5064 / 5073
页数：10
相关论文
共 50 条
  • [21] N-ACYLIMINIUM SALTS FROM THE REACTION OF NITRILIUM SALTS WITH ALDEHYDES
    JOCHIMS, JC
    GLOCKER, MO
    HOFMANN, J
    FISCHER, H
    TETRAHEDRON, 1991, 47 (02) : 205 - 218
  • [22] Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support
    Meester, WJN
    Rutjes, FPJT
    Hermkens, PHH
    Hiemstra, H
    TETRAHEDRON LETTERS, 1999, 40 (08) : 1601 - 1604
  • [23] INTRAMOLECULAR REACTIONS OF ACYCLIC N-ACYLIMINIUM IONS .2. ALLYL SILANES AS NUCLEOPHILES
    HIEMSTRA, H
    FORTGENS, HP
    SPECKAMP, WN
    TETRAHEDRON LETTERS, 1985, 26 (26) : 3155 - 3158
  • [24] INTRAMOLECULAR REACTIONS OF ACYCLIC N-ACYLIMINIUM IONS .1. PROPARGYL SILANES AS NUCLEOPHILES
    HIEMSTRA, H
    FORTGENS, HP
    STEGENGA, S
    SPECKAMP, WN
    TETRAHEDRON LETTERS, 1985, 26 (26) : 3151 - 3154
  • [25] Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
    Grossmann, Oleg
    Maji, Rajat
    Aukland, Miles H.
    Lee, Sunggi
    List, Benjamin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (09)
  • [26] New fused lactones from indolizinediones via N-acyliminium ions
    Othman, M
    Pigeon, P
    Decroix, B
    TETRAHEDRON, 1998, 54 (30) : 8737 - 8744
  • [27] Asymmetric Bronsted Acid Catalyzed Nucleophilic Addition to in situ Generated Chiral N-Acyliminium Ions
    Rueping, Magnus
    Nachtsheim, Boris J.
    SYNLETT, 2010, (01) : 119 - 122
  • [28] Electro-initiated Coupling Reactions of N-Acyliminium Ion Pools with Arylthiomethylsilanes and Aryloxymethylsilanes
    Suga, Seiji
    Shimizu, Ikuo
    Ashikari, Yosuke
    Mizuno, Yusuke
    Maruyama, Tomokazu
    Yoshida, Jun-ichi
    CHEMISTRY LETTERS, 2008, 37 (09) : 1008 - 1009
  • [29] Allylation of exocyclic N-acyliminium ions generated from chiral N-[1-(phenylsulfonyl)alkylloxazolidin-2-ones
    Marcantoni, E
    Mecozzi, T
    Petrini, M
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09): : 2989 - 2994
  • [30] Intramolecular Friedel-Crafts-type reactions involving N-acyliminium ions derived from glycine templates
    Sánchez, JD
    Ramos, MT
    Avendaño, C
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17): : 5731 - 5735
12345