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Mechanochemical Preparation of Hydantoins from Amino Esters: Application to the Synthesis of the Antiepileptic Drug Phenytoin

2014; American Chemical Society; Volume: 79; Issue: 21 Linguagem: Inglês

10.1021/jo5017629

1520-6904

Laure Konnert, Benjamin Reneaud, Renata Marcia de Figueiredo, Jean‐Marc Campagne, Frédéric Lamaty, Jean Martínez, Evelina Colacino,

Synthesis and Characterization of Heterocyclic Compounds

The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.