A rapid and efficient microwave-assisted synthesis of hydantoins and thiohydantoins

Giulio G. Muccioli, Jacques H. Poupaert, Johan Wouters, Bernadette Norberg, Wolfgang Poppitz, Gerhard K E Scriba, Didier M. Lambert

Research output: Contribution to journalArticle

Abstract

The present paper describes studies on the synthesis of the antiepileptic drug phenytoin, and of structurally related derivatives. First, the influence of the solvent has been investigated in the microwave-assisted synthesis of the drug, resulting in a yield improvement and a cleaner reaction. Second, a two-step reaction is described to synthesize selectively and in high yields phenytoin. The first step consists in microwave activation of the reaction of benzil with thiourea, the second step includes the conversion of the resulting 2-thiohydantoin to phenytoin using hydrogen peroxide. Moreover, microwave activation is a very convenient method for the synthesis of 3-alkylated phenytoin derivatives, resulting in a much more selective method than the previously reported procedure using alkylating agents.

Original languageEnglish
Pages (from-to)1301-1307
Number of pages7
JournalTetrahedron
Volume59
Issue number8
DOIs
Publication statusPublished - 17 Feb 2003

Keywords

  • 5-aryl-3-alkyl-imidazolidinediones
  • Microwave activation
  • Phenytoin

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    Muccioli, G. G., Poupaert, J. H., Wouters, J., Norberg, B., Poppitz, W., Scriba, G. K. E., & Lambert, D. M. (2003). A rapid and efficient microwave-assisted synthesis of hydantoins and thiohydantoins. Tetrahedron, 59(8), 1301-1307. https://doi.org/10.1016/S0040-4020(03)00033-4