Syntheses and Chemical Properties of Novel 1,3-Oxathiolan-5-one Derivatives

Abstract

2-Aklylidene-4-arylidene-1 (III-1a-m) and 2,4-diarylidene-l,3-oxathiolan-5-one (III-2a—i) derivatives were synthesized by treating β-aryl-α-mercaptoacrylic acids (I) with alkanoic acid anhydrides (II) or by treating a-acylthio-/i-arylacrylic acids (V) with thionyl chloride in dimethylformamide. Basic hydrolysis and methanolysis of III-1 and III-2 ifl the presence of lithium hydroxide easily occurred to give the corresponding ring-cleaved products, the carboxylic acid (I and II) and the ester (VII and VIII), respectively. The catalytic hydrogenation of the two olefinic bonds of III-2 in the presence of 10% palladium charcoal proceeded easily without ring cleavage to give l,3-oxathiolan-5-one (IXa—e) derivatives. The oxidation of III-l and III-2 with m-chloroperbenzoic acid afforded the corresponding 1,3-oxathiolan-5-one S-oxide (Xa, b) derivatives. © 1985, The Pharmaceutical Society of Japan. All rights reserved.