Chinese Journal of Applied Chemistry ›› 1997, Vol. 0 ›› Issue (5): 5-9.

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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

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