Conversion of reducing carbohydrates into hydrophilic substituted imidazoles

Abstract

Carbohydrates, as cheap mass-products, promise to be outstanding candidates as sustainable raw materials. To achieve the goal of carbohydrate utilisation as industry raw materials, environmental low impact conversions from sugars to high value products are needed. Here we present the conversion of reducing sugars into imidazole heterocycles. Imidazole formation was achieved by a one-pot conversion of reducing mono and disaccharides with amidines in a melt of ammonium carbonate. A range of disaccharides were converted into different 2-substituted imidazoles carrying a varying glycosylation pattern on the 4-tetrahydroxy butyl side chain. All conversions were performed without the need of protecting groups, using benign reagents and solvents.