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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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Publication details

The article was received on 08 Nov 2013, accepted on 16 Dec 2013 and first published on 18 Dec 2013


Article type: Paper
DOI: 10.1039/C3RA47349J
Citation: RSC Adv., 2014,4, 5759-5767

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    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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