Categories: Synthesis of N-Heterocycles >
Synthesis of hydantoins
Name Reactions
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.
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.
