Synthesis of 1,3,4-oxadiazoles from the reaction of N-isocyaniminotriphenylphosphorane (NICITPP) with cyclohexanone,a primary amine and an aromatic carboxylic acid via intramolecular aza-Wittig reaction of in situ generated iminophosphoranes |
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| Authors: | Ali Ramazani Yavar Ahmadi Nadia Fattahi Hamideh Ahankar Mousa Pakzad Hamideh Aghahosseini |
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| Affiliation: | 1. Department of Chemistry, University of Zanjan, Zanjan, Iranaliramazani@gmail.com;3. North West Reseach Complex, Nuclear Science and Technology Research Institute, Bonab, Iran;4. Department of Chemistry, University of Zanjan, Zanjan, Iran;5. Department of Chemistry, Abhar Branch, Islamic Azad University, Abhar, Iran |
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| Abstract: | The 1:1 imine intermediate generated by the addition of a primary amine to cyclohexanone trapped by N-isocyaniminotriphenylphosphorane (NICITPP) in the presence of aromatic carboxylic 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 (18-26°C). The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields. |
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| Keywords: | N-isocyaniminotriphenylphosphorane (NICITPP) cyclohexanone aromatic carboxylic acid 1,3,4-oxadiazole aza-Wittig reaction primary amine |
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