Pseudohalogen chemistry. XI. Some aspects of the chemistry of octhiocyanato-β-dicarbonyl compounds

Article abstract of DOI:10.1016/S0040-4020(01)85248-0

Enolised α-thiocyanato-β-dicarbonyl compounds dimerise in ethanol at room temperature to give tautomeric 4,5-disubstituted 2-amino- and 2-acetamido-thiazoles by a C-S-C + C-N cyclisation. Tautomerism is due to the unusual 4-(β-dicarbonyl-α-thio) substituent. Competing intramolecular cyclisations lead to minor amounts of heterocycles containing the thiazole and/or oxathiole ring systems.