Stereoselective intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction of N-formyl-β-nitroamides

被引:19
|
作者
Kadowaki, Ayako
Nagata, Yoshiaki
Uno, Hidemitsu
Kamimura, Akio [1 ]
机构
[1] Yamaguchi Univ, Dept Appl Mol Biosci, Grad Sch Med, Ube, Yamaguchi 7558611, Japan
[2] Yamaguchi Univ, Dept Appl Chem, Grad Sch Sci & Engn, Ube, Yamaguchi 7558611, Japan
[3] Ehime Univ, Interated Ctr Sci, Matsuyama, Ehime 7908577, Japan
关键词
Michael addition; nitroalkenes; formamide; 1,3-dipolar cycloaddition cyclization;
D O I
10.1016/j.tetlet.2007.01.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective intramolecular nitrile oxide cycloaddition (INOC) reaction was achieved from N-formyl-beta-nitroamides, which were prepared through the Michael addition of allylic formamides to nitroalkenes, and cis-pyrroroisoxazoles and trans-piperidinoisoxazoles were obtained in a stereoselective manner. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1823 / 1825
页数:3
相关论文
共 50 条
  • [21] Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides
    Alcaide, B
    Almendros, P
    Sáez, E
    ARKIVOC, 2004, : 137 - 152
  • [22] A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction
    Bakthadoss, Manickam
    Vinayagam, Varathan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (39) : 10007 - 10014
  • [23] Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides
    Yeh, MCP
    Jou, CF
    Yeh, WT
    Chiu, DY
    Reddy, NRK
    TETRAHEDRON, 2005, 61 (02) : 493 - 500
  • [24] 1,3-Dipolar cycloaddition reaction of N-cyclohexylnitrone
    Chakraborty, B.
    Ghosh, A. R.
    Indian Journal of Chemistry. Section B: Organic and Medicinal Chemistry, 1994, 33 (12):
  • [25] STEREOSELECTIVE INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF CHIRAL CHROMIUM TRICARBONYL COMPLEXED NITRONE
    BALDOLI, C
    DELBUTTERO, P
    LICANDRO, E
    MAIORANA, S
    ALBINATI, A
    TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1711 - 1717
  • [26] A POLYMERIZATION OF ISOPHTHALONITRILE DI-N-OXIDE BY 1,3-DIPOLAR CYCLOADDITION REACTION
    IWAKURA, Y
    AKIYAMA, M
    SHIRAISH.S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1965, 38 (02) : 335 - +
  • [27] 1,3-Dipolar cycloaddition reaction on carbohydrate template: Stereoselective synthesis of glycospiroheterocycles
    Prasanna, R.
    Purushothaman, S.
    Raghunathan, R.
    TETRAHEDRON, 2020, 76 (35)
  • [28] Intramolecular 1,3-dipolar cycloaddition of nitrones to allylsilanes
    Arnold, W
    Mohr, P
    SYNLETT, 1996, (12) : 1215 - &
  • [29] NITRILE N-OXIDE OF FERROCENYLACETIC ACID IN THE REACTION OF 1,3 DIPOLAR CYCLOADDITION
    SHVEKHGEIMER, GA
    ZVOLINSKII, VI
    KOBRAKOV, KI
    KRAPIVIN, AM
    DOKLADY AKADEMII NAUK SSSR, 1980, 252 (03): : 636 - 638
  • [30] 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO METHYLENE STEROIDS
    PARINI, C
    COLOMBI, S
    IUS, A
    LONGHI, R
    VECCHIO, G
    GAZZETTA CHIMICA ITALIANA, 1977, 107 (11-1): : 559 - 563