Synthesis of new imidazolidin-2,4-dione and 2-thioxoimidazolidin-4-ones via C-phenylglycine derivatives.
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.
de Sousa Luis
José Alixandre
JA
Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, João Pessoa-PB, CEP 58.051-970, Brazil.
Barbosa Filho
José Maria
JM
Freitas Lira
Bruno
B
Almeida Medeiros
Isac
I
Soares Lima de Morais
Liana Clébia
LC
dos Anjos
Raline Mendonça
RM
Dos Santos
Alexsandro Fernandes
AF
Soares de Oliveira
Cledualdo
C
de Athayde-Filho
Petrônio Filgueiras
PF
D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013867:Thiohydantoins / Q000138:chemical synthesis* / Q000737:chemistry
D048289:Imidazolidines; D013867:Thiohydantoins; C514490:imidazolidine-2,4-dione; C008852:2-phenylglycine; D005998:Glycine