Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones |
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Authors: | Reddy Y Suman Pal A P John Gupta Preeti Ansari Alafia A Vankar Yashwant D |
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Affiliation: | Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. |
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Abstract: | Azidation of 1,2-anhydro sugars with NaN(3) in CH(3)CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range. |
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