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Issue 10, 2013
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Conversion of reducing carbohydrates into hydrophilic substituted imidazoles

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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.

Graphical abstract: Conversion of reducing carbohydrates into hydrophilic substituted imidazoles

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Article information


Submitted
21 Jun 2013
Accepted
03 Sep 2013
First published
03 Sep 2013

Green Chem., 2013,15, 2993-2998
Article type
Paper

Conversion of reducing carbohydrates into hydrophilic substituted imidazoles

A. Brust and E. Cuny, Green Chem., 2013, 15, 2993
DOI: 10.1039/C3GC41203B

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