• Title/Summary/Keyword: Iminophosphorane

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

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Karimi, Zahra;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2700-2704
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    • 2011
  • 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.

Efficient and Selective Construction of Pyrrolo[3,2-d]pyrimidine Derivatives

  • He, Ping;Wu, Jing;Hu, Yang-Gen;Li, Zai-Fang;Hou, Qiu-Fei;Wang, Yan-Ling;Zhao, Kun;Zhang, Erli
    • Bulletin of the Korean Chemical Society
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    • v.35 no.2
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    • pp.617-621
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    • 2014
  • An efficient and selective method for the synthesis of ethyl 2-amino/aryloxy-3-aryl-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylate derivatives has been developed. The main process involved the reaction of diethyl 1-phenyl-3-((triphenylphosphoranylidene)amino)-1H-pyrrole-2,4-dicarboxylate and aromatic isocyanates, followed by addition of amines/phenols in the presence of catalytic amount of sodium ethoxide or solid potassium carbonate.