Synthesis of new imidazolidin-2,4-dione and 2-thioxoimidazolidin-4-ones via C-phenylglycine derivatives

Molecules. 2009 Dec 30;15(1):128-37. doi: 10.3390/molecules15010128.

Abstract

Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70-74%. The mass, infrared, (1)H and (13)C-NMR spectra of representative products are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Imidazolidines / chemical synthesis*
  • Imidazolidines / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Thiohydantoins / chemical synthesis*
  • Thiohydantoins / chemistry

Substances

  • Imidazolidines
  • Thiohydantoins
  • imidazolidine-2,4-dione
  • 2-phenylglycine
  • Glycine