Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

  • Received : 2011.06.05
  • Accepted : 2011.06.29
  • Published : 2011.08.20
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Abstract

The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by N-isocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

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References

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