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In the reaction of ethyl isothiocyanatoacetate with diamines, followed by cyclization of the intermediate product, 3-monosubstituted thiohydantoins have been obtained. It was found that the reaction course depends on the purity of the isothiocyanate used and also, in the case of dialkylaminoamines, the self-cyclization occurs. Besides the dialkylamino derivatives of 3-monosubstituted 2-thiohydantoins also new monoalkylamino, amino and heterocyclic derivatives were synthesized. The aryldiazonium derivative of 3-monosubstituted 2-thiohydantoin yielded both respective phenol derivative after hydrolysis and the product of coupling with 2-naphthol.

Some ethyl 5-aryl(or benzyl)-2-oxo-1,3,4-oxadiazole-3(2H)-acetates were prepared and treated with ammonia, primary amines or hydrazine to give 1-amino-2,4-imidazolidinedione or 1,3-diamino-2,4-imidazolidinedione derivatives. The 1,3-bis(benzylideneamino)-,2,4-imidazolidinedione was obtained by reacting ethyl bromoacetate with the 1,5-dibenzylidenecarbonohydrazide sodium salt

New derivatives of the naturally occurring amino acid 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (spinacine) are reported. These include amide, ester, 5-alkyl and acyl, and regiospecific N im -alkyl and aralkyl derivatives. Synthesis via the Pictet-Spengler reaction of N im -substituted histidines is described. Cyclic hydantoin derivatives of spinacines are included

Eight new fluorine containing arylglyoxals have been synthesized by the oxidation of the active methyl group of fluorinated acetophenones by selenium dioxide in dioxan-water medium. The corresponding hydrates were obtained by dissolving arylglyoxals in minimum amounts of benzene and adding hot water. Seventeen new fluorine containing 1,5-disubstituted hydantoins were subsequently prepared by the condensation of these arylglyoxals with arylureas in ethanol and characterized by ir, pmr and mass spectral studies. Representative compounds have been screened for their possible anticonvulsant and analgesic activities. None of the compounds show significant analgesic acitivity.