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A study on the regiospecificity of the base-catalyzed reaction of activated -oxo- nitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetra- hydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic consider- ations could be formed, were not observed. Spectroscopic and experimental evidence, to- gether with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.

Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives