Studies on the Syntheses and Antibacterial Activity of Thiohydantoin Related Compounds. X. : Reaction of 1-Phenyl-2-thiohydantoins and Hydrazine hydrate.

Abstract

Application of hydrazine hydrate to the aqueous suspension of ethyl 3-phenyl-4-thiohydantoates (IV to VI) and 1-phenyl-2-thiohydantoins (VII to IX) afforded 3-phenyl-4-thiohydantoic acid hydrazides (X to XII). When the reaction was carried out by heating in ethanol, desulfurization occurred in compounds VII to IX to produce 1-phenyl-2-hydrazinohydantoins (XVIII to XX), although the compounds IV, V, and VI reacted in the same way as above to form X, XI, and XII. Heating of X, XI, and XII in acetic anhydride resulted in their cyclization to VII, VIII, and IX, respectively. Application of several aromatic aldehydes to X and XVIII afforded hydrazones. Growth-inhibiting action of these compounds against tubercle bacilli was examined.