Base‐induced cycloadditions of tosylmethyl isocyanide to a series of isothiocyanates have been investigated. Depending on the reaction conditions, thiazoles 5 and/or imidazoles 7 are obtained, with the thiazoles, in particular, being obtained with high regiospecificity. During the course of this work a high‐yield ring transformation of 5‐amino‐1,3‐thiazoles (5) to imidazole‐5‐thiols (7) was discovered, which has not been previously reported. A number of reactions of 7 are described.
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