Paper
4- And 5-hydroxylaminothiazolidine-2-thiones. Acylation, synthesis, and structural investigation of new 6-thioxo(oxo) derivatives of 4,5-dihydro-6H-1,2,5-thiadiazine
Published Sep 1, 1987 · T. I. Orlova, S. Epshtein, A. F. Rukasov
Chemistry of Heterocyclic Compounds
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Abstract
The treatment of 4- and 5-hydroxylaminothiazolidine-2-thiones as well as 5-hydroxylaminothiazolidin-2-one with acetic anhydride or benzoyl chloride is accompanied, as a rule, by the formation of O-acyl derivatives. The 4-(O-acyl) derivatives are thereby either stable to thermal or alkaline treatment, or are converted to 4-iminothiazolidine-2-thione; the 5-(O-acetyl)-hydroxylamines rearrange to 6-thioxo(oxo) derivatives of 4,5-dihydro-6H-1,2,5-thiadiazine.
This study demonstrates that acetic anhydride or benzoyl chloride treatment of 4- and 5-hydroxylaminothiazolidine-2-thiones leads to stable O-acyl derivatives, which can be converted to 4-iminothiazolidine-2-thione or 6-thioxo(
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