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 |
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Authors: | Ali Ramazani Fatemeh Zeinali Nasrabadi Yavar Ahmadi |
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Affiliation: | 1. Chemistry Department, Zanjan University, P.O. Box 45195‐313, Zanjan, Iran, (phone: +98‐241‐5152572;2. fax: +98‐241‐5152477);3. Young Researchers Club, Zanjan Branch, Islamic Azad University, Zanjan, Iran |
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Abstract: | 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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Keywords: | Chloroacetone Phosphorane, (N‐isocyanoimino)triphenyl‐ 1,3,4‐Oxadiazoles aza‐Wittig reaction Multicomponent reactions X‐Ray crystallography |
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