Chemistry of sulfonyl isocyanates and sulfonyl isothiocyanates.XI. Cyclizations with epoxides

Autor:	L. M. Frey, J. W. Mcfarland, J. J. Beaulieu, L. N. Arrey
Rok vydání:	1988
Předmět:	Sulfonyl chemistry.chemical_classification Organic Chemistry Epoxide Ether Hydrochloric acid Medicinal chemistry Isocyanate chemistry.chemical_compound Hydrolysis chemistry Sodium hydroxide Styrene oxide Organic chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 25:1431-1434
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570250532
Popis:	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 6 M 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-toluene-sulfonyl)-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°.
Databáze:	OpenAIRE
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