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 y-ketoamides (11a—c), while that of 7a—c led to the formation of 5-hydroxypyrrolidones (12a—c). © 1986, The Pharmaceutical Society of Japan. All rights reserved.