Synthesis and antimicrobial activity of some new 2,5-imidazolidinediones.

1,3-Diphenyl-4-thione-2,5-imidazolidinedione (3) was reacted with amino compounds and o-diamines to give 1,3-diphenyl-4-substituted imino-2,5-imidazolinediones (4a-m) and 1,3-diphenyl-1H-imidazo[4,5-b]quinoxaline-2(3H)-ones (5a-c), respectively. Condensation of 3 with hydrazines afforded the corresponding hydrazone derivatives (6a-c). Reaction of 6a with acetyl chloride, aromatic aldehydes, arylsulphonyl chlorides, phthalic acid anhydrides and isocyanates or thiocyanates furnished 6d, furnished the acetyl-amido derivative 6b, the benzylidenimino derivatives 7a-d, the arylsulphonamido derivatives 8a-b, the phthalimido derivatives 9a-b and the ureido and thioureido derivatives 10a-b, respectively. Again compound 3 was reacted with n-butylmagnesium bromide or diazomethane to give the dibutyl derivative 12 or 13.