A simple nitration of electrophilic alkenes with tetranitromethane in the presence of triethylamine. Synthesis of functionalized β-nitroalkenes

被引:6
作者
Volkova, Yulia A. [1 ]
Averina, Elena B. [1 ,2 ]
Grishin, Yuri K. [1 ]
Rybakov, Victor B. [1 ]
Kuznetsova, Tamara S. [1 ,2 ]
Zefirov, Nikolai S. [1 ,2 ]
机构
[1] Lomonosov Moscow State Univ, Dept Chem, Moscow 119992, Russia
[2] IPhaC RAS, Chernogolovka 142432, Moscow Region, Russia
基金
俄罗斯基础研究基金会;
关键词
Tetranitromethane; Electrophilic alkenes; beta-Nitroalcohols; beta-Nitroalkenes; DIELS-ALDER; CONJUGATED NITROALKENES; BETA(2)-AMINO ACIDS; NITRO ACRYLATES; NITROACRYLATES; CONVERSION; CYCLOADDITIONS; CHEMISTRY; REAGENT; OLEFINS;
D O I
10.1016/j.tetlet.2011.04.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method for the preparation of functionalized beta-nitroalkenes based on the nitration of alpha,alpha-di- and alpha,alpha,beta-trisubstituted unsaturated aldehydes, ketones and esters with tetranitromethane in the presence of triethylamine is described. Series of substituted beta-nitroalcohols and beta-nitroalkenes are obtained in good yields under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2910 / 2913
页数:4
相关论文
共 37 条
  • [1] ALTUKHOV KV, 1976, USP KHIM+, V45, P2050
  • [2] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)
    Ballini, R
    Petrini, M
    [J]. TETRAHEDRON, 2004, 60 (05) : 1017 - 1047
  • [3] β-Nitroacrylates as an Emerging, Versatile Class of Functionalized Nitroalkenes for the Synthesis of a Variety of Chemicals
    Ballini, R.
    Gabrielli, S.
    Palmieri, A.
    [J]. CURRENT ORGANIC CHEMISTRY, 2010, 14 (01) : 65 - 83
  • [4] β-Nitroacrylates as Key Starting Materials for the Uncatalysed One-Pot Synthesis of Polyfunctionalized Dihydroquinoxalinone Derivatives, via an anti-Michael Reaction
    Ballini, Roberto
    Gabrielli, Serena
    Palmieri, Alessandro
    [J]. SYNLETT, 2009, (06) : 965 - 967
  • [5] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS
    BARRETT, AGM
    GRABOSKI, GG
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 751 - 762
  • [6] Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates
    Blanco-Ania, Daniel
    Hermkens, Pedro H. H.
    Sliedregt, Leo A. J. M.
    Scheeren, Hans W.
    Rutjes, Floris P. J. T.
    [J]. TETRAHEDRON, 2009, 65 (27) : 5393 - 5401
  • [7] BUEGGEMANN M, 2003, J AM CHEM SOC, V125, P15284
  • [8] From nature, through chemical synthesis, toward use in agriculture: Oryzoxymycin case study
    Bwire, Regina N.
    Majinda, Runner R.
    Masesane, Ishmael B.
    Steel, Patrick G.
    [J]. PURE AND APPLIED CHEMISTRY, 2009, 81 (01) : 105 - 112
  • [9] Asymmetric Diels-Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation
    Calmes, Monique
    Escale, Francoise
    Didierjean, Claude
    Cazals, Guillaume
    Martinez, Jean
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (20) : 2491 - 2496
  • [10] Synthesis and X-ray crystal structure of (-)-calicheamicinone
    Clive, DLJ
    Bo, YX
    Selvakumar, N
    McDonald, R
    Santarsiero, BD
    [J]. TETRAHEDRON, 1999, 55 (11) : 3277 - 3290