Formations of various schiff base from dialdofuranose derivatives

In this work, firstly dialdofuranose derivatives were synthesized by the oxidation of α-chloralose andβ-chloralose. Than, the condensation reaction of these dialdofuranose derivatives were examined withamines as 1,4-phylenediamine, amine, 2,6-dichloro-nitroaniline and aniline and hydrazin as 2,4-dinitrophenylhydrazine and it has been worked that the synthesis of Schiff bases and hydrazonederivatives on skeleton of sugar molecules.Schiff bases couldn?t be achieved by condensation of amines with dialdofuranose derivatives.Therefore, synthesis of dialdofuranose derivative of β-chloralose with 2,4- dinitrophenylhydrazine wasstudied and 1,2-O-(S)-trichloroethylidene-α-D-xylo-1,4-furanodialdose-2,4-dinitrophenylhydrazone wassynthesized.At the different study, 3-O-methyl-1,2-O-(S)-trichloroethylidene-α-D-gulucofuranose (13) wassythesized from β-chloralose and then this formation was converted to the dialdofuranose derivative.This compound was treated with 2,4- dinitrophenylhydrazine and benzylamine and the compound of 3-O-Methyl-1,2-O-(S)-trichloroethylidene-α-D-xylo-1,4-furanodialdose-2,4-dinitrophenyldrazone (15) andthe compound of 3-O-Methyl-1,2-O-(S)-trichloroethylidene-α-D-xylo-1,4-furanodialdose-benzylimine(16) were sythesized.Same studies were performed for α-chloralose. Firstly, 5 and 6-OH groups of α-chloralose wereprotected and then, 3-O-methyl-1,2-O-(R)-trichloroethylidene-α-D-gulukofuranose (19) derivative withmethylation of 3-OH group was sythesized in order to obtain the related dialdofuranose derivative.The reaction of the sythezied compoud (19) with 2,4-dinitrophenylhydrazine was studied and thecompound of 3-O-methyl-1,2-O-(R)-trichloroethylidene-α-D-xylo-1,4-furanodialdose-2,4-dinitrophenylhydrazone (21) was synthesized.Key words: Hydrazone, Imines, Schiff bases.