Synthesis of New Imidazolidin-2,4-dione and 2-Thioxoimidazolidin-4-ones via C-Phenylglycine Derivatives

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, 1H and 13C-NMR spectra of representative products are discussed.

Keywords

• hydantoins
• C-phenylglycine
• imidazolidines
• 2-thioxoimidazolidine-4-ones