Studies on thiazolidin-4-ones. V. The mode of action of hydrazines on 5-arylmethylenethiazolidine-2,4-diones

Abstract

Hydrazine hydrate reacts with 5-arylmethylenethiazolidine-2,4-diones (1a-c) to give mixtures of the N-hydrazinocarbonyl-2- hydrazonopropanamides (3a-c) and the 6-arylmethyl-3-hydrazino-1,2,4- triazin-5(2H)-ones (4a-c). The thiazolidinedione (1c) reacts with methylhydrazine to give a semisolid from which it is possible to isolate the 2-methylhydrazone (3d). Phenylhydrazine attacks(1a) to give a mixture of (4d) and 6-benzyl-2-phenyl-3-phenylazo-1,2,4-triazin- 5(2H)-one (5a).However, (1b) and (1c) give mixtures of (3f) and 6-(4- methoxybenzyl)-2-phenyl-1,2,4-triazine-3,5(2H,4H)-dione (6), and (3e) and (5b) respectively. N-Methyl-N-phenylhydrazine reacts with (1b)to give 2-mercapto-3-(4-methoxyphenyl)-N-(N-methide(2).The structures of all of these products are confirmed by analytical as well as spectral data, and the route of these transformations is discussed.