A Simple One-Pot Dehydration Process to Convert N-acetyl-D-glucosamine into a Nitrogen-Containing Compound, 3-acetamido-5-acetylfuran

An efficient process for converting N‐acetyglucosamine (NAG) into 3‐acetamido‐5‐acetylfuran (3A5AF) is reported. 3A5AF is proposed as an N‐containing platform chemical, which contains renewable nitrogen. In the reported method NAG, in the presence of boric acid (B(OH)3) and sodium chloride (NaCl), p...

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Bibliographic Details
Published in:ChemSusChem 2012-09, Vol.5 (9), p.1767-1772
Main Authors: Omari, Khaled W., Dodot, Linda, Kerton, Francesca M.
Format: Article
Language:English
Subjects:
Acetamides - chemistry
Acetylglucosamine - chemistry
amines
biomass
carbohydrates
Catalysis
Chlorine - chemistry
Furans - chemistry
homogeneous catalysis
Kinetics
Solvents - chemistry
Temperature
Water - chemistry
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Summary:An efficient process for converting N‐acetyglucosamine (NAG) into 3‐acetamido‐5‐acetylfuran (3A5AF) is reported. 3A5AF is proposed as an N‐containing platform chemical, which contains renewable nitrogen. In the reported method NAG, in the presence of boric acid (B(OH)3) and sodium chloride (NaCl), produces 58 % yield 3A5AF in dimethylacetamide under microwave irradiation (220 °C, 15 min). A maximum yield of 62 % was obtained in the presence of 4 equivalent NaCl. Performing ICP–MS analysis on NAG from different chemical suppliers highlighted the importance of Cl and B levels in this process. Trace impurities are, therefore, important considerations in biomass transformations. This solution‐phase process produces approximately 30 times more 3A5AF than a pyrolysis route reported previously. Harbor not Haber Nitrogen: An amido‐substituted furan can be obtained in up to 58 % yield through heating an amino‐sugar, which can be obtained from fishery waste, in the presence of NaCl and boric acid. The product represents a structural motif within biologically active natural products.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201200113