Electrochemical oxidation–cyclocondensation of chitin-derived 3-acetamido-5-acetylfuran (3A5AF) for the synthesis of 3-acetyl-4-acetamidopyrrolin-2-ones

Abstract

Chitin, an abundant biopolymer, is a valuable source of biogenic nitrogen and ideal for producing organonitrogen compounds with a low carbon footprint. Among its derivatives, 3-amidofurans are key small-molecule platforms. This study demonstrates that 3-acetamido-5-acetylfuran (3A5AF), derived from chitin, undergoes anodic oxidation in the presence of methanol to yield a 3-acetamido-2,5-dimethoxydihydrofuran. This synthon facilitates the synthesis of 3-acetyl-4-acetamidopyrrolin-2-ones (21 examples) upon reaction with various primary amines under eco-friendly conditions at ambient temperature.