Simple and facile electrocatalytic approach to medicinally relevant spirocyclopropylpyrazolones directly from pyrazoline-5-ones and activated olefins
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  • 作者:Michail N. Elinson ; Evgeniya O. Dorofeeva…
  • 关键词:Electrocatalysis ; Cascade reaction ; Undivided cell ; Pyrazoline ; 5 ; ones ; Activated olefins ; Spirocyclopropylpyrazolones
  • 刊名:Research on Chemical Intermediates
  • 出版年:2016
  • 出版时间:March 2016
  • 年:2016
  • 卷:42
  • 期:3
  • 页码:2191-2200
  • 全文大小:472 KB
  • 参考文献:1.L.A. Wessjohann, W. Brandt, Chem. Rev. 103, 1625 (2003)CrossRef
    2.F. Brackmann, A. de Meijere, Chem. Rev. 107, 4538 (2007)CrossRef
    3.C. Laroche, J.-B. Behr, J. Szymoniak, P. Bertus, C. Schutz, P. Vogel, R. Plantier-Royon, Bioorgan, Med. Chem. 14, 4047 (2006)CrossRef
    4.V.P. Sandanayaka, A.S. Prashad, Y. Yang, R.T. Williamson, Y.I. Lin, T.S. Mansour, J. Med. Chem. 46, 2569 (2003)CrossRef
    5.T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T.Y.-H. Wub, Y. He, Bioorg. Med. Chem. Lett. 16, 2105 (2006)CrossRef
    6.T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Tuntland, K. Zhang, D. Karanewsky, Y. He, Bioorg. Med. Chem. Lett. 16, 2109 (2006)CrossRef
    7.S. Devi, A. Nayak, A.S. Mittra, J. Indian Chem. Soc. 61, 640 (1984)
    8.M. Itokawa, T. Miyata, M. Arai, Eur. Pat. Appl. EP 2 189 537 A1 (2010)
    9.J. Elguero, in ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scrive. Comprehensive Heterocyclic Chemistry II, vol 3 (Pergamon-Elsevier Science, Oxford, 1996)
    10.R. Frankle, R.D. Little, Chem. Soc. Rev. 43, 2492 (2014)CrossRef
    11.Y.N. Ogibin, M.N. Elinson, G.I. Nikishin, Russ. Chem. Rev. 78, 89 (2009)CrossRef
    12.M.N. Elinson, E.O. Dorofeeva, A.N. Vereshchagin, G.I. Nikishin, Russ. Chem. Rev. 84, 485 (2015)CrossRef
    13.G.I. Nikishin, M.N. Elinson, S.K. Feducovich, Russ. Chem. Bull. 35, 1749 (1986)CrossRef
    14.M.N. Elinson, T.L. Lizunova, M.O. Dekaprilevich, Y.T. Struchkov, G.I. Nikishin, Mendeleev Commun. 3, 192 (1993)CrossRef
    15.M.N. Elinson, A.N. Vereshchagin, N.O. Stepanov, T.A. Zaimovskaya, V.M. Merkulova, G.I. Nikishin, Tetrahedron Lett. 51, 428 (2010)CrossRef
    16.M.N. Elinson, S.K. Feducovich, N.O. Stepanov, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron 64, 708 (2008)CrossRef
    17.M.N. Elinson, S.K. Feducovich, T.L. Lizunova, G.I. Nikishin, Tetrahedron 56, 3063 (2000)CrossRef
    18.A.N. Vereshchagin, M.N. Elinson, T.A. Zaimovskaya, G.I. Nikishin, Tetrahedron 64, 9766 (2008)CrossRef
    19.A.N. Vereshchagin, M.N. Elinson, E.O. Dorofeeva, R.F. Nasybullin, I.S. Bushmarinov, A.S. Goloveshkin, M.P. Egorov, Electrochim. Acta 165, 116 (2015)CrossRef
    20.M.N. Elinson, S.K. Feducovich, Z.A. Starikova, O.S. Olessova, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron Lett. 41, 4937 (2000)CrossRef
    21.M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, G.I. Nikishin, Tetrahedron 60, 11743 (2004)CrossRef
    22.M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, S.V. Gorbunov, G.I. Nikishin, Tetrahedron Lett. 46, 6389 (2005)CrossRef
    23.M.N. Elinson, S.K. Feducovich, Z.A. Starikova, A.N. Vereshchagin, G.I.P.A. Belyakov, Nikishin, Tetrahedron 62, 3989 (2006)CrossRef
  • 作者单位:Michail N. Elinson (1)
    Evgeniya O. Dorofeeva (1)
    Anatoly N. Vereshchagin (1)
    Alexander D. Korshunov (1)
    Mikhail P. Egorov (1)

    1. N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, 119991, Moscow, Russia
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Catalysis
    Physical Chemistry
    Inorganic Chemistry
  • 出版者:Springer Netherlands
  • ISSN:1568-5675
文摘
The electrolysis of pyrazoline-5-ones and activated olefins in the presence of sodium bromide as mediator in alcohols in an undivided cell results in efficient formation of the substituted spirocyclopropylpyrazolones in 50–85 % yields. This novel electrocatalytic process opens a convenient way to functionalized spirocyclopropylpyrazolones—the promising compounds for the different biomedical applications. Thus, the simple electrocatalytic system can produce in an undivided cell under mild conditions the electrochemically induced cascade reaction of pyrazoline-5-ones with activated olefins.
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