Synthesis of 3-aminomethyl-4-hydroxycoumarins and their retro-Mannich reaction in dimethyl sulfoxide
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  • 作者:B. G. Milevskii ; T. A. Chibisova ; N. P. Solov′eva…
  • 关键词:4 ; hydroxycoumarin derivatives ; imines ; enamines ; hydrogenation ; aminomethylcoumarins ; retro ; Mannich reaction ; dicoumarol
  • 刊名:Russian Chemical Bulletin
  • 出版年:2015
  • 出版时间:February 2015
  • 年:2015
  • 卷:64
  • 期:2
  • 页码:423-428
  • 全文大小:331 KB
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  • 作者单位:B. G. Milevskii (1)
    T. A. Chibisova (1)
    N. P. Solov′eva (1)
    A. Yu. Sukhorukov (2)
    V. F. Traven (1)

    1. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation
    2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Chemistry
    Organic Chemistry
    Inorganic Chemistry
    Russian Library of Science
  • 出版者:Springer New York
  • ISSN:1573-9171
文摘
Hydrogenation of 3-formyl-4-hydroxycoumarin aliphatic imines leads to 3-aminomethyl-4-hydroxycoumarins, which undergo a retro-Mannich reaction in dimethyl sulfoxide containing even traces of water. Keywords 4-hydroxycoumarin derivatives imines enamines hydrogenation aminomethylcoumarins retro-Mannich reaction dicoumarol

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