Ring Transformation of 2-Furylcarbamates to 5-Hydroxy-3-pyrrolin-2-ones

Abstract

N-Ethoxycarbonyl- and N-benzyloxycarbonyl-5-hydroxy-5-methoxyalkylpyrrolinones (6a-c) and (7a-c) together with minor products 8-10 were obtained from the photooxidation or autoxidation of corresponding 2-furylcarbamates (4a-c) and (5a-c). The catalytic hydrogenation of 6a-c afforded saturated γ-ketoamides (11a-c), while that of 7a-c led to the formation of 5-hydroxypyrrolidones (12a-c).