Reaction of 2-thiohydantoins with some diazoalkanes and some amines

Reaction of 2-thiohydantoin derivatives with diazoalkanes as diazomethane. diphenyldia-zomethane and/or 9-diazofluorene was investigated. Several 2-thio- and 2-methylthiohydantoins (IIa,6), (IIIa,b), (XI) and (XII) were prepared via the reaction of 2-thiohydantoins (Ia,b) and (X) with diazomethane. 2-Morpholino- and/or 2-piperidino- glycocyamidines (VIIa,b) and (XVa,b) were prepared by reacting 2-alkylthiohydantoins (IIIa) and (XII), respectively, with morpholine and/or piperidine. Moreover, treating of two equivalents of XIVa-d wi th one equivalent of piperazine afforded 1,4[di-(5-phenylmethylene-hydantoinyl)]-piperazines (XVIa,b). The behaviour of 2-alkylthiohydantoins towards alanine and anthranilic acid was also investigated. The structure of the products was established by correct analytical and spectral data as well as by chemical evidencies.