Categories: Synthesis of N-Heterocycles >

Synthesis of hydantoins

Name Reactions

Bucherer-Bergs Reaction

---

Recent Literature

1,5-Disubstituted hydantoins/thiohydantoins have been synthesized in good yield by a microwave-promoted solvent-free condensation of arylglyoxals and phenylurea/thiourea using polyphosphoric ester (PPE) as a reaction mediator. The workup is simple and involves treatment with ice-cold water.
S. Paul, M. Gupta, R. Gupta, A. Loupy, Synthesis, 2002, 75-78.

Enantiomerically pure hydantoins are prepared from optically pure α-amino amides utilizing triphosgene. A mechanism for the racemization observed with 1,1'-carbonyldiimidazole (CDI) for this type of reaction is proposed.
D. Zhang, X. Xing, G. D. Cuny, J. Org. Chem., 2006, 71, 1750-1753.

Copper acetate promoted N-arylation of imides with boronic acids can be employed as a major method for the synthesis of N₃-aryl hydantoins.
H. M. Hügel, C. J. Rix, K. Fleck, Synlett, 2006, 2290-2292.