Synthesis Of New 1,2,3-Triazole And 1,2,3-Triazoline Derived From Unsaturated D-Fructose Via 1,3-Dipolarcyclo addition Reaction

Hussain K. Sharba, Abdul

	Synthesis Of New 1,2,3-Triazole And 1,2,3-Triazoline Derived From Unsaturated D-Fructose Via 1,3-Dipolarcyclo addition Reaction
Al-Mustansiriyah Journal of Science
Article 1, Volume 22, Issue 2, 2011, Pages 109-122
Author
Abdul Hussain K. Sharba
Abstract
This work describes synthesis of new fructofuranosyl derivatives containing 1,2,3-triazole ring, 1,2,3-triazoline ring or tetrazole ring derived from unsaturated D-fructose via 1,3-dipolar cycloaddition reaction. 1,3,4,6-tetra-O-benzoyl--D-fructo furanose (1) was prepared as starting material , to synthesize sugar derivatives (2-4). The 1,3-dipolar cycloaddition reaction of vinylic sugar (4) and aryl sulfonyl azides gave sugar based spiro heterocyclic derivatives (5-7). Cycloaddition reaction was also carried out with two sugar derivatives with an exo unsaturated bond (8 and 12) and aryl sulfonyl azides. The triazole derivatives (9-11) and triazoline derivatives (13-15) successfully obtained. Moreover, the reaction of the azidosugar (3) with (8) in presence of (ph3P)3CuI as catalyst afforded a triazole with two substituted sugar residues (16). The prepared compounds were identified by spectroscopic methods; IR, FT-IR, UV, 1HNMR AND 13CNMR. Antibacterial and antifungal activities of some of the synthesized compounds were studied and compared with that of two antibiotics (Ampicillin and Gentamycin). The activities were determined in vitro using disc diffusion method against Staph. aureus, Eschericha coli and three pathogenic strains of yeast (Candida) and fungus (Aspergillus flaveus and Penicillium spp.). The results revealed that some of the studied compounds showed measurable activity. The minimal inhibitory concentration (MIC) have been also studied to determine the low concentration for inhibition.

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