Synthesis , characterization and study biological activity of some new five heterocyclic derivatives for β-D-Fructopyranose

Abstract

This research involves the synthesis of some new 1,2,3-Traizoliene and 1,2,3,4-Tetrazole derivatives. Firstly was converted 2-aminpyridine to thiazolo[4,5-b]pyridin-2-amine (A) by reacting with ammonium thiocyanate in presence of glacial acetic acid. Then, compound (B) was prepared from the reaction of (A)with p-acetamido benzenesulphonyl chloride in basic medium. Hydrolysis of compound (B) in glacial acetic acid gives compound (C).Shiff bases (1-5) were prepared by reaction of (C) with aromatic aldehydes . Compound (D) was synthesized from reaction of compound (C) with acetic anhydride in presence of Conc. H2SO4 . Chalcone derivatives (6-10) were prepared from reaction compound (D) with aromatic aldehyde. Finally To achieve this work , Methyl- D- fructpyranoside (E) was synthesized by treating D-Fructose with Methanol in acidic medium under thermodynamically controlled conditions to make sure that the fructopyranoside are the predominant product. The hydroxyl group on C1 was converted into mesylester derivatives (F) by reaction (E) with one equivalent of mesylchloride at 0Co The vital compound in this synthesis compound (G) was obtained by treatment (F) with one mole of sodium azide in presence of TBAB. Reaction (G)with Schiff bases gives1,2,3,4-Tetrazole derivatives ( 11-15 ),while reaction with unsaturated compound formed 1,2,3-Traizoliene derivatives (16-20) . The synthesized compounds have been measured by their melting points, and characterized by C.H.N. analysis, FT-IR and 1H-MNR spectroscopy.