Cu–Al mixed oxide-catalysed multi-component synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives

Abstract

A series of carbohydrate-linked 1,2,3-triazole derivatives were synthesized in good yields from glucofuranose and allofuranose diacetonides using as key step a three-component 1,3-dipolar azide–alkyne cycloaddition catalysed by a Cu–Al mixed oxide. In this multi-component reaction, Cu–Al mixed oxide/sodium ascorbate system serves as a highly reactive, recyclable and efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The reported protocol has significant advantages over classical CuI/N,N-diisopropylethylamine (DIPEA) or CuSO4/sodium ascorbate conditions in terms of efficiency and reduced synthetic complexity. In addition, the selective deprotection of synthesized di-O-isopropylidene derivatives was also carried out leading to the corresponding mono-O-isopropylidene products in moderate yields. Some of the synthesized triazole glycoconjugates were tested for their in vitro antimicrobial activity using the disc diffusion method against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), as well as fungus (Aspergillus niger) and yeast (Candida utilis). The results revealed that these compounds exhibit moderate to good antimicrobial activity mainly against Gram-negative bacteria.

Keywords

• glycoconjugates
• 1,2,3-triazole
• multi-component reaction
• cu–al mixed oxide
• biological activity