Unlocking the Potential of Bio‐Based Nitrogen‐Rich Furanic Platforms as Biomass Synthons

Abstract

The demand for new biomass‐derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5‐hydroxymethylfurfural are cornerstones of sustainable chemistry, 3‐acetamido‐5‐acetyl furan (3A5AF), an N‐rich furan obtained from chitin biomass, remains unexplored, due to the poor reactivity of the acetyl group relative to previous furanic aldehydes. Here we developed a reactive 3‐acetamido‐5‐furfuryl aldehyde (3A5F) and demonstrated the utility of this synthon as a source of bio‐derived nitrogen‐rich heteroaromatics, carbocycles, and as a bioconjugation reagent.

Catalytic conversion of chitin-based biomass to nitrogen-containing chemicals

“…Furthermore, they achieved the two-step dehydration-oxidative cleavage of NAG to obtain 3A5F. 101 In the first step, NAG was reacted in pyridine with boric acid and triflic acid at 116°C for 30 min. During the second step, water and NaIO 4 were added, and the reaction took place at RT for 1.5 h. An overall yield of 92% 3A5F was obtained under optimal conditions.…”

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Figure 6 The downstream upgrading of 3A5F into various organonitrogen compounds Reprinted with permission from ref. 101 . Copyright 2023 Wiley.

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