Studies on the Syntheses and Antibacterial Activity of Thiohydantoin Related Compounds. XII. : Syntheses of Alkyl Compounds of 5-Benzylidene-2-thiohydantoins and 2-Substituted-5-benzylidenehydantoin Compounds.

Abstract

Starting with 5-(p-chlorobenzylidene)-2-thiohydantoin and 5-(p-methoxybenzylidene)-2-thiohydantoin, their monoalkyl (II to IX or II' to IX') and dialkyl compounds (X to XVII) (R=CH₃, C₂H₅, n-C₃H₇, n-C₄H₉) were prepared. Heating of these compounds with conc. hydrochloric acid afforded 3-alkyl-5-benzylidenehydantoins (XVIII to XXVII), and reaction with acetic anhydride have acetylated compounds (XXVIII to XXXI). Reaction with hydrazine hydrate afforded hydrazino compounds (XXXIV to XXXVII). Reaction with phenylhydrazine and some amines was also carried out and 2-substituted compounds (XL to XLIII) were prepared. Growth-inhibiting action of these compounds against tubercle bacclli was examined.