Efficient synthesis of 2,3,4-trisubstituted furans from the reaction of activated acetylenes with ethyl bromopyruvate in the presence of enaminones

被引:0
|
作者
Issa Yavari
Zinatossadat Hossaini
Maryam Sabbaghan
机构
[1] Tarbiat Modares University,Chemistry Department
关键词
Ethyl bromopyruvate; Activated acetylenes; Trisubstituted furans; Enaminone.;
D O I
暂无
中图分类号
学科分类号
摘要
The reaction of dialkyl acetylenedicarboxylates or diaroylacetylenes with ethyl bromopyruvate in the presence of enaminones led to 2-ethyl 3,4-dialkyl 4-bromo-4,5-dihydro-2,3,4-furantricarboxylates or ethyl 3,4-diaroyl-4-bromo-4,5-dihydro-2-furancarboxylate in excellent yields. These compounds are quantitatively converted to the corresponding 2,3,4-trisubstituted furans by 4-dimethylaminopyridine.
引用
收藏
页码:945 / 948
页数:3
相关论文
共 50 条
  • [41] Preparation of 2,3,4-trisubstituted piperidines by a formal hetero-ene reaction of amino acid derivatives
    Laschat, S
    Frohlich, R
    Wibbeling, B
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08): : 2829 - 2838
  • [42] Preparation of 2,3,4-Trisubstituted Piperidines by a Formal Hetero-Ene Reaction of Amino Acid Derivatives
    Laschat, S.
    Froehlich, R.
    Wibbeling, B.
    Journal of Organic Chemistry, 61 (08):
  • [43] Asymmetric Synthesis of 2,3,4-Trisubstituted Functionalised Tetrahydrofurans via an Organocatalytic Michael Addition as Key Step
    Enders, Dieter
    Wang, Chuan
    Greb, Andreas
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 987 - 992
  • [44] An efficient highly regioselective synthesis of 2,3,4-trisubstituted pyrroles by cycloaddition of polarized ketene S,S- and N,S-acetals with activated methylene isocyanides
    Misra, N. C.
    Panda, K.
    Ila, H.
    Junjappa, H.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04): : 1246 - 1251
  • [45] An Unexpected Synthesis of 2,3,4-Trisubstituted Quinolines from Imino-Isatin and Acetylenic Esters Catalyzed by Pyridine as an Organocatalyst
    Afkham, Amir Arian
    Mokhtari, Javad
    Haghighi, Ali Javaheri
    Yavari, Issa
    CHEMISTRYSELECT, 2018, 3 (31): : 9159 - 9161
  • [46] Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles:: A formal total synthesis of lukianol A
    Liu, JH
    Yang, QC
    Mak, TCW
    Wong, HNC
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3587 - 3595
  • [47] Facile and convenient synthesis of 2,4-disubstituted and 2,3,4-trisubstituted 1,3-thiazoles
    Hassan, Alaa A.
    Mohamed, Shaaban K.
    Mohamed, Nasr K.
    El-Shaieb, Kamal M. A.
    Abdel-Aziz, Ahmed T.
    Mague, Joel T.
    Akkurt, Mehmet
    JOURNAL OF SULFUR CHEMISTRY, 2016, 37 (02) : 162 - 175
  • [48] A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction
    Kalmode, Hanuman P.
    Vadagaonkar, Kamlesh S.
    Murugan, Kaliyappan
    Chaskar, Atul C.
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (06) : 4631 - 4639
  • [49] A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities
    Zapol'skii, Viktor A.
    Kaul, Sandra
    Karge, Bianka
    Broenstrup, Mark
    Gjikaj, Mimoza
    Kaufmann, Dieter E.
    MOLECULES, 2023, 28 (06):
  • [50] A convenient synthesis of novel 2,3,4-trisubstituted 1,5-benzothiazepines bearing a sulfonyl pharmacophore
    Karale, Sanjay N.
    Pratap, Umesh R.
    Mahalle, Shital R.
    Mane, Ramrao A.
    JOURNAL OF SULFUR CHEMISTRY, 2011, 32 (04) : 303 - 309