Tetrahedron

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

…, S Dabbs, RG Guy, AA Mahomed, P Mountford

Index: Atkins, Elaine F.; Dabbs, Steven; Guy, Robert G.; Mahomed, Akbar A.; Mountford, Philip Tetrahedron, 1994 , vol. 50, # 24 p. 7253 - 7264

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Citation Number: 18

Abstract

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 CSC+ CN 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