5‐Ethoxy‐3‐(trichloromethyl)‐1,2,4‐oxadiazole

doi:10.1002/JHET.5570030222

Paper

5‐Ethoxy‐3‐(trichloromethyl)‐1,2,4‐oxadiazole

Published Jun 1, 1966 · V. Narayanan, J. Bernstein

Journal of Heterocyclic Chemistry

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1

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Abstract

5-Ethoxy-3-(trichloromethyl)-1, 2, 4-oxadiazole (V) was synthesized to elucidate the chemistry involved in the preparation of the hitherto unreported alkoxy-1, 2, 4-oxadiazoles and to determine the effect of the isosteric replacement of sulfur by oxygen on antifungal activity. Heating the “amino-oxime” tautomer II of trichloroacetamidoxime with ethyl chloroformate furnished exclusively the O-acylated product III. The trans configuration of III accounts for its resistance to cyclize under a variety of conditions, in contrast to the general behaviour of acylated amidoximes. Pyrolysis of III at 160° yielded IV which exists in the keto form. Refluxing IV with ethyl iodide in the presence of silver oxide gave an isomeric mixture which was separated by v.p.c. to give V and VI. Compound V retained 60% of the overall activity of the corresponding sulfur analog.

Study Snapshot

5-Ethoxy-3-(trichloromethyl)-1,2,4-oxadiazole (V) shows 60% of the antifungal activity of its sulfur analog, making it a promising new antifungal agent.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

5‐Ethoxy‐3‐(trichloromethyl)‐1,2,4‐oxadiazole

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