129200-06-2Relevant academic research and scientific papers
Solid-phase synthesis of 3,5-disubstituted 1,3-oxazolidin-2-ones by an activation/cyclo-elimination process
Ten Holte, Peter,Thijs, Lambertus,Zwanenburg, Binne
, p. 7407 - 7410 (1998)
Polymer-supported sulfonyl chloride is used in the solid-phase synthesis of disubstituted 1,3-oxazolidin-2-ones. The target compounds were prepared by attaching 1,2-diols to the solid support, followed by reaction with p- toluenesulfonyl isocyanate and su
Chemistry of Sulfonyl Isocyanates and Sulfonyl Isothiocyanates. XI. Cyclizations with Epoxides
McFarland, J. W.,Beaulieu, J. J.,Arrey, L. N.,Frey, L. M.
, p. 1431 - 1434 (2007/10/02)
4-Toluenesulfonyl isocyanate cyclized with 1,2-epoxy-3-phenoxypropane and 2,3-epoxypropyl 4-methoxyphenyl ether, respectively, to give 3-(4-toluenesulfonyl)-5-phenoxymethylene-2-oxazolidone (I) and 3-(4-toluenesulfonyl)-5-(4-methoxyphenoxymethylene)-2-oxazolidone (II).Compounds I and II were hydrolyzed in 2 M sodium hydroxide solution to the corresponding uncyclized hydroxy amides, VII and VIII.Compound I was remarkably stable toward 6M hydrochloric acid and amines.Styrene oxide, 1,2-epoxybutane, 3-chloro-1,2-epoxypropane, and 1-methoxy-2-methylpropylene oxide reacted with the isocyanate to afford 3-(4-toluenesulfonyl)-4-phenyl-2-oxazolidone (III), 3-(4-toluenesulfonyl)-4-ethyl-2-oxazolidone (IV), 3-(4-toluenesulfonyl)-5-chloromethyl-2-oxazolidone (V), and 3-(4-toluenesulfonyl)-4,4-dimethyl-5-methoxy-2-oxazolidone (VI), respectively.The yield of VI was constant over a temperature range of 25-90 deg.
