A Simple and Highly Efficient One-Pot Procedure for the Synthesis of Amides via Beckmann Rearrangements Using 1-Tosylimidazole (TsIm) |
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| Authors: | Mohammad Navid Soltani Rad Ali Khalafi-Nezhad Somayeh Behrouz Zohreh Amini Marzieh Behrouz |
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| Institution: | 1. Department of Chemistry , Faculty of Basic Sciences, Shiraz University of Technology , Shiraz, Iran;2. Department of Chemistry , College of Sciences, Shiraz University , Shiraz, Iran |
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| Abstract: | A facile and highly efficient method for one-pot Beckmann rearrangement of ketoximes into N-substituted amides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, ketoximes are refluxed with TsIm and Cs2CO3 in the presence of SiO2 as a recyclable catalyst in DMF affording the corresponding amides in high yields. This methodology is highly efficient and regioselective for various structurally diverse ketoximes including symmetrical and unsymmetrical as well as cyclic oximes. The results of quantum mechanical studies used to rationalize the experimental outcomes are discussed. |
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| Keywords: | Amide Beckmann rearrangement ketoxime SiO2 N-(p-toluenesulfonyl)imidazole (TsIm) |
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