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

Azidation of 1,2-anhydro sugars with NaN3 in CH3CN 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.