Methyl, phenyl and 1‐alkenyl isothiocyanates 1 can react with diazomethane to give the corresponding 5‐amino‐1,2,3‐thiadiazoles 4. In the presence of an excess of diazomethane these thiadiazoles rearrange to 1‐substituted‐5‐(methylthio)‐1H‐1,2,3‐triazoles 3. Reaction of 1‐alkenyl isothiocyanate 1a with hydrazoic acid yields the corresponding 5‐(1‐alkenylamino)‐1,2,3,4‐thia‐triazole 11, which does not rearrange when treated with diazomethane.
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Hoff et al. (1974) studied this question.
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