Tetrahedron p. 7253 - 7264 (1994)
Update date:2022-08-05
Topics:
Atkins, Elaine F.
Dabbs, Steven
Guy, Robert G.
Mahomed, Akbar A.
Mountford, Philip
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.
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