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3,4-Disubstituted-1,2,4-oxadiazole-5(4H)-ones were obtained from the reaction of substituted amide oximes with ethylchloroformate. These compounds were treated with P2S5 to give corresponding 1,2,4-oxadiazole-5-thiones. Rearrangement of 1,2,4-oxadiazole-5-thiones, catalysed by metallic copper, yielded 1,2,4-thiadiazole-5-ones. The reaction of 1,2,4-thiadiazole-5-ones with P2S5 gave 1,2,4-thiadiazole-5-thiones.
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Ağirbaş et al. (1998) studied this question.
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