Synthesis of thiazoles and imidazoles from isothiocyanates and tosylmethyl isocyanide. Base‐induced ring transformation of 5‐amino‐1,3‐thiazoles to imidazole‐5‐thiols
- 1 January 1982
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 101 (1) , 28-34
- https://doi.org/10.1002/recl.19821010102
Abstract
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.Keywords
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