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One-Pot, Four-Component Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives from (Isocyanoimino)triphenylphosphorane, a Primary Amine, an Aromatic Carboxylic Acid, and Chloroacetone

  作者 Ramazani, A; Nasrabadi, FZ; Ahmadi, Y  
  选自 期刊  Helvetica Chimica Acta;  卷期  2011年94-6;  页码  1024-1029  
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[摘要]The 1 : 1 imine intermediate 7 generated by the addition of a primary amine 2 to chloroacetone (1) is trapped by (isocyanoimino)triphenylphosphorane (4) in the presence of an aromatic carboxylic acid 3 and leads to the formation of the corresponding iminophosphorane intermediate 9 (Scheme 2). The 1,3,4-oxadiazole derivatives 5 are then formed via an intramolecular aza-Wittig reaction of the iminophosphorane intermediate 9. The reactions were completed under neutral conditions at room temperature. The fully substituted 1,3,4-oxadiazole derivatives 5 were produced in high yields (Table).

 
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