Synthesis of Thiazolid-2:5-Dione

Abstract

RECENT interest in the synthesis of polypeptides has centred around the ability of oxazolid-2 : 5-dione and its 3- and 4-substituted derivatives to polymerize with loss of carbon dioxide or to condense with amino-acids or their esters. Cook and Levy¹ have now shown that the analogous 2-thiothiazolid-5-one and its 4-methyl derivative may also be used for the introduction of glycyl or alanyl residues. Attempts by Cook, Heilbron and Hunter² to obtain the structural cross of the above heterocycles, that is, thiazolid-2 : 5-dione (III), were unsuccessful. These authors were interested in the latter compound and its derivatives, as they considered they would be of a stability intermediate between that of oxazolid-2 : 5-dione and 2-thiothiazolid-5-one and would consequently be more easily handled. The parent compound has now, unexpectedly, been obtained in good yield by the accompanying reaction scheme.