Related Experiment Video
Updated: Aug 7, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N-Acetylglucosamine into Unsubstituted
Changqu Lin1, Hao Yang1, Xin Gao1
1College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, 211816, P. R. China.
Abstract:
Aminofurans are widely used in drug synthesis as aromatic modules analogous to aniline. However, unsubstituted aminofuran compounds are difficult to prepare. In this study, a process for the selective conversion of N-acetyl-d-glucosamine (NAG) into unsubstituted 3-acetamidofuran (3AF) is developed. The yield of 3AF from NAG catalyzed by a ternary Ba(OH)2 -H3 BO3 -NaCl catalytic system in N-methylpyrrolidone at 180 °C for 20 min can reach 73.9 %. Mechanistic studies reveal that the pathway to 3AF starts with a base-promoted retro-aldol condensation of the ring-opened NAG, affording the key intermediate N-acetylerythrosamine. Judicious selection of the catalyst system and conditions enables the selective conversion of biomass-derived NAG into 3AF or 3-acetamido-5-acetylfuran.
More Related Videos
11:06GC-based Detection of Aldononitrile Acetate Derivatized Glucosamine and Muramic Acid for Microbial Residue Determination in Soil
Published on: May 19, 2012
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Related Concept Videos
Acid-Catalyzed Aldol Addition Reaction
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Base-Catalyzed Aldol Addition Reaction
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation