December 2023
Synthesis of New Imidazolidin-2,4-dione and 2-Thioxoimidazolidin-4-ones via C-Phenylglycine Derivatives
José Alixandre De Sousa Luis,José Maria Barbosa Filho,Bruno Freitas Lira,Isac Almeida Medeiros,Liana Clébia Soares Lima de Morais,Alexsandro Fernandes Dos Santos,Cledualdo Soares de Oliveira andPetrônio Filgueiras De Athayde-Filho
1Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, João Pessoa – PB, CEP 58.051-970, Brazil
2Centro de Educação e Saúde, Unidade Acadêmica de Saúde, Universidade Federal de Campina Grande, Cuité – PB, CEP 58.175-000, Brazil
3Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa – PB, CEP 58059-900, Brazil
*Author to whom correspondence should be addressed.
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