中华医学超声杂志

应用化学 ›› 1997, Vol. 0 ›› Issue (5): 5-9.

• 研究论文 • 上一篇    下一篇

1,3-偶极环加成反应在杂螺环化合物合成中的应用

冯亚青1, 张晓东2, 张卫红1, 周维义3   

  1. 1. 天津大学应用化学系, 天津 300072;
    2. 天津大学制药厂;
    3. 天津大学分析中心, 天津
  • 收稿日期:1997-01-13 修回日期:1997-07-10 出版日期:1997-10-10 发布日期:1997-10-10
  • 基金资助:
    国家教委留学回国人员科研基金

Application of 1,3-Dipolar Cycloaddtion in Synthesis of Spiroheterocycles

Feng Yaqing1, Zhang Xiaodong2, Zhang Weihong1, Zhou Weiyi3   

  1. 1. Department of Applied Chemistry, Tianjin University, Tianjin 300072;
    2. Pharmaceutical Factory, Tianjing;
    3. Analysis Center, Tianjin University, Tianjin
  • Received:1997-01-13 Revised:1997-07-10 Published:1997-10-10 Online:1997-10-10

PDF

521

摘要： 氧化腈与4,4-亚甲基-1-甲基哌啶的1,3-偶极环加成反应生成了杂螺[4.5]葵烷化合物,反应具有立体专一性。产物经LiAlH4还原生成了γ-氨基醇,最后经插入C-1单元扩环生成了新的杂螺[5.5]十一烷化合物

关键词: 偶极环加成, 杂螺环化合物, 合成

Abstract: A series of heterospiro compounds were synthsized by 1,3-dipolar cycloaddition of nitrile oxides to 4,4-methylene-1-methylpiperidine. NMR study showed that only one stereoioisomer was formed selectively. In the consecutive step these were cleaved by hydrogenolysis to γ-amino-alcohols, which in a final step were recyclized by insertion of a C-1 unit, giving the target structure.

Key words: dipolar cycloaddition, spiro-heterocycle, synthesis

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