Bromodimethylsulfonium bromide (BDMS)-mediated Lossen rearrangement: synthesis of unsymmetrical ureas |
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| Authors: | Deepak K Yadav Arvind K Yadav Vishnu P Srivastava Geeta Watal Lal Dhar S Yadav |
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| Institution: | 1. Alternative Therapeutics Unit, Drug Development Division, Medicinal Research Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India;2. Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India |
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| Abstract: | Bromodimethylsulfonium bromide (BDMS) was found to be a very efficient reagent for Lossen rearrangement of hydroxamic acids to the corresponding isocyanates which were subsequently trapped in situ with various amines to afford unsymmetrical ureas in good to excellent yields (64–89%). The protocol is experimentally simple, mild, and represents valuable alternative to the existing methods for in situ activation of hydroxamic acids promoting Lossen rearrangement. |
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