Abstract
2-Thiohydantoin derivatives are produced by heating a mixture of thiourea and an alpha-amino acid. The method described offers the advantages of simplicity, low cost, easy work-up and scalability.
Highlights
Thiohydantoins are sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups [1]
The methods developed for combinatorial synthesis and used to prepare 2-thiohydantoin derivatives in small quantities for purposes like biological testing may not be feasible when operated on a large scale [22d,24]
We report a simple method for the preparation of 2-thiohydantoin derivatives that can be scaled up in the laboratory
Summary
Thiohydantoins are sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups [1]. It is not surprising that various different synthetic methods have been developed to prepare 2-thiohydantoin and its derivatives. Other preparative methods for 2-thiohydantoins include the reactions between thiourea and benzil [17], Molecules 2006, 11 thiourea and α-halo acids [18], oxazolinone and thiocyanate [19], amino amide and diimidazole thiocarbonate [20], and others [21]. The above methods often suffer from one or more synthetic limitations for large-scale preparation of 2-thiohydantoin derivatives due to their use of expensive, moisture sensitive and/or highly toxic starting materials and reagents. The methods developed for combinatorial synthesis and used to prepare 2-thiohydantoin derivatives in small quantities for purposes like biological testing may not be feasible when operated on a large scale [22d,24]. We report a simple method for the preparation of 2-thiohydantoin derivatives that can be scaled up in the laboratory
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