Thiation of new 5-(2-aryl-2-oxoethyl)-2,4-dioxo-1, 3-thiazolidines

Abstract

The hitherto unknown 5-(2-aryl-2-oxoethyl)-3-substituted-2,4-dioxo-1,3-thiazolidines 2 and 5-(2-aryl-2-oxoethylidene)-3-aryl-2,4-dioxo-1,3-thiazolidines 4 have been prepared from their 2-thioxo- homologues 1 and 3, respectively, via treatment with CrO₃. Compound 4 has also been obtained by treating 1 and/or 2 with bromine at different experimental conditions. Thiation of 2 and/or 4, gave a mixture of 3,5-di-substituted-2,3-dihydro-2-oxothieno[2,3-d]thiazoles 5 and the respective 2-thioxo derivatives 6. Reactions of hydrazine hydrate with 1c, d, were carried out at room temperature as well as under reflux, affording di-(3-oxo-6-aryl-4,5-dihydropyridazin)disulfides 7c, d and di-(3-oxo-6-arylpyridazin)disulfides 8c, d, respectively, together with 4-arylthiosemi carbazides 9c, d, under both conditions. Structures of the above products have been elucidated based on their microanalytical and spectroscopic data. Compound 2e exhibited pronounced antischistosomal activity.

Keywords:

• transformation
• 2,4-thiazolidinones
• thieno-thiazoles
• antischistosomal