Synthesis in the Diazasteroid Group. XX. Synthesis of the 5,14-Diazasteroid System(Organic,Chemical)

  • 的場 勝英
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
  • 平井 美朗
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
  • 時沢 実
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
  • 涌井 優子
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
  • 永田 正典
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University
  • 山崎 高應
    Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

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説明

trans-2-Quinolizidinone (I) was treated with methyl 2-pyrrolidylacetate (III) to give a mixture of two isomers, 5,14-diaza-1,6-cyclo-1,10-secogon-8-en-11-one (IV) and 5,14-diazagon-8-en-11-one (Va) in 8.6 and 2.7% yields, respectively. 1,2,3,3a,4,5,6,7,8,9-Decahydro-7-benzoylpyrrolo[1,2-α]-[1,6]-naphthyridin-5-one (VIb) [prepared from 1-benzoyl-4-piperidone (IIb) and III] was hydrolyzed and then allowed to react with methyl vinyl ketone to give a Michael adduct (VId). It was treated with mercuric acetate to afford regio- and stereoselectively 5,14-diazagon-8-ene-2,11-dione (Vb), whose angular protons at the C_<10> and C_<13> were anti to each other. The structure of Vb was determined by X-ray crystallographic analysis. Compound Vb was converted to Va via a thioketai (Vc).

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詳細情報 詳細情報について

  • CRID
    1571980077232130560
  • NII論文ID
    110006280876
  • NII書誌ID
    AA00602100
  • ISSN
    00092363
  • 本文言語コード
    en
  • データソース種別
    • CiNii Articles

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