Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N-Acetylglucosamine into Unsubstituted 3-Acetamidofuran by Retro-Aldol Condensation

Aminofurans are widely used in drug synthesis as aromatic modules analogous to aniline. However, unsubstituted amino-furan 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)-H3BO3-NaCl catalytic system in N-methylpyrrolidone at 180 degrees 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.

Automated summary

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)-H3BO3-NaCl catalytic system in N-methylpyrrolidone at 180 degrees 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.