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

Brust, Andreas and Cuny, Eckehard (2014) Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles. RSC Advances, 4 11: 5759-5767. doi:10.1039/c3ra47349j

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Author Brust, Andreas
Cuny, Eckehard
Title Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles
Journal name RSC Advances   Check publisher's open access policy
ISSN 2046-2069
Publication date 2014
Year available 2013
Sub-type Article (original research)
DOI 10.1039/c3ra47349j
Open Access Status Not Open Access
Volume 4
Issue 11
Start page 5759
End page 5767
Total pages 9
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2014
Language eng
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.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
Institute for Molecular Bioscience - Publications
 
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