Sìntese de amidas heterocíclicas derivadas do naproxeno
Data
2022-12-16
Autores
Morine, Caroline Rangel [UNIFESP]
Orientadores
Reis, Adriana Karla Cardoso Amorim [UNIFESP]
Tipo
Trabalho de conclusão de curso de graduação
Título da Revista
ISSN da Revista
Título de Volume
Resumo
O atual trabalho visa à síntese de amidas heterocíclicas derivadas de Naproxeno. Essas amidas foram preparadas através da reação dos anti-inflamatório com aminas aromáticas heterocíclicas (imidazol, 3-amino-1,2,4-triazol e 2-aminotiazol) por diferentes metodologias a partir de reações de acoplamento via DIC, DCC, EDC e/ou 1,1’ - carbonildiimiazol (CDI). Uma abordagem alternativa “ambientalmente amigável” também foi explorada, onde houve a substituição do diclorometano pelo dimetilcarbonato. As amidas derivadas de AINEs foram sintetizadas com sucesso, com rendimentos dentro de uma faixa satisfatória, de moderados a ótimos. Através do estudo metodológico realizado foi visto que o EDC e o CDI se comportaram como os melhores reagentes de acoplamento, enquanto que a adição de DMF como co-solvente na reação, auxilia de modo positivo para elevar o rendimento. A abordagem alternativa de substituição do diclorometano por dimetilcarbonato foi eficaz para todos os casos
The current work aims at the synthesis of heterocyclic amides derived from Naproxen. These amides were prepared through the reaction of anti-inflammatory with heterocyclic aromatic amines (imidazole, 3-amino-1,2,4-triazole and 2-aminothiazole) by different methodologies from coupling reactions via DIC, DCC, EDC and /or 1,1'-carbonyldiimiazole (CDI). An alternative “environmentally friendly” approach was also explored, replacing dichloromethane with dimethylcarbonate. NSAID-derived amides have been successfully synthesized, with yields within a satisfactory moderate to optimal range. Through the methodological study carried out, it was seen that EDC and CDI behaved as the best coupling reagents, while the addition of DMF as a co-solvent in the reaction, positively helps to increase the yield. The alternative approach of replacing dichloromethane with dimethylcarbonate was effective in all cases. .
The current work aims at the synthesis of heterocyclic amides derived from Naproxen. These amides were prepared through the reaction of anti-inflammatory with heterocyclic aromatic amines (imidazole, 3-amino-1,2,4-triazole and 2-aminothiazole) by different methodologies from coupling reactions via DIC, DCC, EDC and /or 1,1'-carbonyldiimiazole (CDI). An alternative “environmentally friendly” approach was also explored, replacing dichloromethane with dimethylcarbonate. NSAID-derived amides have been successfully synthesized, with yields within a satisfactory moderate to optimal range. Through the methodological study carried out, it was seen that EDC and CDI behaved as the best coupling reagents, while the addition of DMF as a co-solvent in the reaction, positively helps to increase the yield. The alternative approach of replacing dichloromethane with dimethylcarbonate was effective in all cases. .