Abstract
This work describes the synthesis of a new fructofuranosyl derivatives comprising1,2,3-triazole, 1,2,3-triazoline or tetrazole ringsvia 1,3-dipolar cycloaddition reaction.To obtain these derivatives, 1,3,4,6-tetra-O-benzoyl-β-D-fructofuranose (1) with free hydroxyl group at position-2 was prepared asthestarting material. Reaction of compound (1) with 45% HBr solution in glacial acetic acid gave compound (2). The bromide (2) was then made to react with some nucleophiles (NaN3and KCN) to give 1,3,4,6-tetra-O-benzoyl-β-D-fructofuranosyl azide (3)and 1,3,4,6-tetra-O-benzoyl-β-D-fructofuranosyl cyanide (4).Treatment of compound (3) with cinnamic acid, cinnamaldehyde, acrylic acid, acrylonitrile, acrylamide and maleic anhydride, gave the triazoline derivatives (5-10).Cycloaddition reaction was also carried out withpropargyl chloride, propargyl alcohol and 1-hexyn-3-ol using (ph3P)3CuI as a catalyst to give the triazole derivatives (12-14).Reactionof the cyanosugar (4) with arylsulfonyl azides gave the tetrazole derivatives (16-18).Antibacterial and antifungal activities of some novelsynthesized compounds were studied and compared with that of two well known antibiotics (Ampicillin and Gentamycin)