Synthesis and Characterization of Amino Acid-Derived Hydantoins

  • Ee-Zhen Chin Tunku Abdul Rahman University College
  • Siow-Ping Tan Tunku Abdul Rahman University College
  • Sook-Yee Liew University of Malaya
  • Thomas Kurz Heinrich-Heine Universität Düsseldorf
Keywords: Alanine; glycine; phenylalanine; hydantoins; Urech hydantoin synthesis

Abstract

The Urech hydantoin synthesis is the chemical reaction of amino acids with potassium cyanate and hydrochloric acid, which allows access to hydantoins and its derivatives. Most of them are biologically active with varieties of structural diversity that make them synthetically attractive. A series of hydantoins were synthesized from various α-amino acids in a reaction with hydrochloric acid and ethanol as the first step, and with potassium cyanate as the second step for the formation of ureido derivatives. Lastly, the cyclization of ureido derivatives yielded the desired hydantoin products. All hydantoins were obtained in a good yield and fully characterized by NMR and IR spectroscopy. This strategy provides a variety of biologically significant hydantoin derivatives.

Published
2021-06-30