Conversion of N‐Acetyl‐D‐glucosamine into 3‐Acetamido‐5‐acetylfuran Using Cheap Ammonium Chloride as Catalyst. Issue 15 (19th April 2022)

• Record Type: Journal Article
• Authors: Wang, Chengyong; Wu, Chaoqiang; Zhang, Alei; Chen, Kequan; Cao, Fei; Ouyang, Pingkai
• Is Part Of: ChemistrySelect. Volume 7:Issue 15(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-19
• Subjects: N-acetyl-D-glucosamine -- 3-acetamido-5-acetylfuran -- ammonium chloride -- Organocatalysis -- Crystal engineering; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202104574
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Herein, we propose a facile method for converting N ‐acetyl‐D‐glucosamine (NAG) into the N‐containing chemical 3‐acetamido‐5‐acetylfuran (3A5AF) using chloride salt as a catalyst. Screening of various chloride salts showed that NH4 Cl possessed the optimal catalytic performance. The catalyst NH4 Cl led to a 3A5AF yield of 43 mol % with LiCl as an additive in N, N ‐dimethylformamide (DMF) solvent at 160 °C for 5 min. Moreover, the solvent, catalyst and additive could be reused at least five times with residual catalytic activity of 94.42 %. Additionally, scaling up of the 3A5AF preparation could be easily realized and the purity of the product 3A5AF reached >99 % purity with 45 mol % isolated yield after a simple isolation procedure. This work provides an environmentally friendly and mild method for converting NAG into 3A5AF. Abstract : This is the first report on converting N ‐acetyl‐D‐glucosamine (NAG) into the 3‐acetamido‐5‐acetylfuran (3A5AF) using inexpensive ammonium chloride as a catalyst. A maximum 3A5AF yield of 43 % can be obtained within 5 min via conventional heating at 160 °C. Moreover, N, N ‐dimethylformamide (DMF), NH4 Cl and LiCl showed good recyclability within five cycles.The high‐purity 3A5AF (>99 %) can be easily obtained using extraction and crystallization.