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Issue 11, 2014
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Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles

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Abstract

The existential importance of a sustainable economy necessitates the utilisation of plant based renewable resources such as lignin and carbohydrates. Carbohydrate utilization as industrial raw materials requires low environmental impact conversions from sugars to high value products. Here we present the conversion of reducing disaccharides into industrially relevant heterocycles of the quinoxaline-, 1,2,4-triazine-, pyrazine- and pyrazolo[3,4-b]quinoxaline-type. Heterocycle formation was facilitated by chemical conversion of reducing sugars into 1,2-dicarbonyl intermediates and their subsequent cyclization with nitrogen bis-nucleophiles. A range of disaccharides was converted into quinoxalines carrying a diverse glycosylation pattern on the polyhydroxy alkyl side chain. All transformations were performed without the need of protecting group chemistry.

Graphical abstract: Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles

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Article information


Submitted
08 Nov 2013
Accepted
16 Dec 2013
First published
18 Dec 2013

RSC Adv., 2014,4, 5759-5767
Article type
Paper

Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles

A. Brust and E. Cuny, RSC Adv., 2014, 4, 5759
DOI: 10.1039/C3RA47349J

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