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Synthesis of hydantoins

Name Reactions

Recent Literature

Reaction of carbodiimides with α-Br(Cl)-aryl acetic acids produces N,N′-substituted 5-arylhydantoins under very mild conditions and high yields. When the carbodiimides are generated in situ by Staudinger reaction, the process becomes a one-pot, three-component sequential synthesis of libraries of differently substituted 5-arylhydantoins.
F. Olimpieri, A. Volonterio, M. Zanda, Synlett, 2008, 3016-3020.

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.

A novel intermolecular α-amination process of esters using CuCl as catalyst and di-tert-butyldiaziridinone as nitrogen source forms hydantoins effectively under mild reaction conditions.
B. Zhao, H. Du, Y. Shi, J. Am. Chem. Soc., 2008, 130, 7220-7221.

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.