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Synthesis and characterization of various amino acid derived thiohydantoins
1 , 2 , * 3
1  Faculty of Science, University of Kragujevac, Radoja Domanovića 12 P.O. Box 60, 34000 Kragujevac, Serbia
2  Faculty of Medical Sciences, University of Kragujevac, Svetozara Markovica 69, 34000 Kragujevac, Serbia
3  Institute for Information Technologies Kragujevac, Department of Science, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia


Hydantoins and their sulfur containing analogues, thiohydantoins, are cyclic ureides that have attracted huge attention ever since their discovery. Most of them are biologically active compounds and several points of structural diversity have made them very synthetically attractive.

Although substituents can be introduced to the hydantoin nucleus, most substituted hydantoins are synthetized from substrates already containing these groups, while forming the hydantoin nucleus. This is a common route to the synthesis of hydantoins and one of them is employed in this study.

A series of 3-allyl-2-thiohydantoins is synthetized from various α-amino acids in a reaction with allyl isothiocyanate. The substitution of the acquired thiohydantoin depends on the structure of the starting α-amino acid. The residual group of the α-amino acid becomes the substituent at the C5-position, while N-monosubstituated amino acids give rise to a subtituent in the N1-position. The reaction is carried out in a two-step process and the reaction conditions generally depend on the nature of the amino acid itself. All thiohydantoins are obtained in a good yield and fully characterized by NMR and IR spectroscopy, as well as X-ray crystallography.

Keywords: thiohydantoin; synthesis; amino acids; substitution