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Abstract 2-(1H-Benzo[d][1,2,3]triazol-1-yl)acetonitrile (2) was prepared in 61% yield by treating benzotriazole (1) with chloroacetonitrile in DMF and in the presence of potassium carbonate. Tetrazole 3 was prepared in 61% yield by treating of the nitrile derivative 2 with sodium azide. Ester 4 was prepared in 67% yield by treating of the tetrazole derivative 3 with ethyl chloroacetate in dry acetone and potassium carbonate. The acetohydrazide 5 was synthesized by hydrazinolysis of the corresponding ester 4 in ethanol at reflux temperature (Scheme 1). Benzylidene derivatives 11-15 were prepared by refluxing of the hydrazide 5 with aromatic aldehyde derivatives 6-10 in ethanol and in the presence of a catalytic amount of glacial acetic acid (Scheme 2). The hydrazide derivative 5 was condensed with D-(+)-Xylose in the presence of a catalytic amount of glacial acetic acid under reflux afforded the corresponding sugar hydrazone 16 in 75% yield. The O-acetyl sugar hydrazone 17 was prepared in 70% yield by treating of the sugar hydrazone 16 with acetic anhydride in pyridine at room temperature. The oxadiazoline derivative 18 was prepared in 90% yield by treating of the sugar hydrazone 16 with acetic anhydride at boiling temperature (Scheme 3). N N N 5 N N N N O H2NHN Scheme 3 AcOH/EtOH/Reflux N N N 16 N N N N O NH N D-Xylose OH HO OH OH Ac2O Pyridine r.t. Ac2O Reflux N N N 17 N N N N O NH N OAc AcO OAc OAc N N N 18 N N N N N N O Ac OAc AcO OAc OAc The hydrazide derivative 5 was condensed with D-(+)-Glucose in the presence of a catalytic amount of glacial acetic acid under reflux afforded the corresponding sugar hydrazone 19 in 92% yield. The O-acetyl sugar hydrazone 20 was prepared in 95% yield by treating of the sugar hydrazone 19 with acetic anhydride in pyridine at room temperature. |