Studies on the synthesis of certain sulphur compounds as antimicrobials, antishistosoma and Molluscidies

ABSTRACT

Interaction of 3, 3-dimercapto-1-[2-thienyl]-2-propen-1-one [I] with alkylhalides, acid chloride gave the S, S-disubstituted derivatives [II, IV], condensation of [I] with aldehydes afforded different products according to the reagent used. In concentrated hydrochloric acid it gives the dithioacetals [V]; while in glacial acetic acid, the chalcone [VI] was the unexpected product. Sulphurization of [I] with P4S10 afforded 5 [2-thienyl]-1,2-dithiacyclopenten-3, thione [VII] in a satisfactory yield; while bromination of [VII], followed by boiling in water gave 5 [2-thienyl]-1, 2-dithiacyclopenten-3-one [IV]. Bromination of [IX] yielded the 4-bromoderivative [X] which on treating with methanolic potassium hydroxide hydrolyses and through interreaction, 2, 5-di [2-thienyl]-1, 4-dithiacyclohexadiene-3, 6-dicarboxylic methylester [IX] was collected. Desulphurization of [XV] followed by alkaline hydrolysis gave 2, 4-di [2-thienyl] thiophene 3, 5-dicarboxylic acid [XVIII]. Oxidative cyclization of furfurylidene thiosemicarbazone gave 2-amino-5 [2-furyl]-1, 3, 4- thiadiazole [XIX] which on treating with isocyanates; namely, naphthyl, and/or cyclohexyl gave the disubstituted ureas [XX]. Condensation of disubstituted urea derivative with bromoethylacetate or/and chloroacetyl chloride obtained the imidazolidinone derivative [XXI], while with dibromoethane yielded the hedantoin derivative [XXII], screening of most derivatives showed activities