Banca de QUALIFICAÇÃO: IVAN MARTINS BARRETO

Uma banca de QUALIFICAÇÃO de DOUTORADO foi cadastrada pelo programa.
STUDENT : IVAN MARTINS BARRETO
DATE: 30/08/2023
TIME: 09:00
LOCAL: online
TITLE:

SYNTHESIS OF TRIAZOLE-PHTHALIMIDE DERIVATIVES CONJUGATED TO PYRIMIDINE BASES WITH ANTIVIRAL POTENTIAL

KEY WORDS:

phthalimide, pyrimidine bases, click reaction, 1,2,3-triazole

PAGES: 209
BIG AREA: Ciências Exatas e da Terra
AREA: Química
SUBÁREA: Química Orgânica
SPECIALTY: Síntese Orgânica
SUMMARY:

The cycloaddition reaction between an organic azide and a terminal alkyne catalyzed by copper - Cu(I) has been the main synthetic route to obtain the 1H-1,2,3-triazole 1,4-disubstituted isomer. Triazoles have great versatility, with application in several areas, with emphasis on medicinal chemistry. The azido-alkyne cycloaddition reaction, also known as the click reaction, has numerous advantages, such as simplicity, fast, good yields, and regioselectivity. In this work, the cycloaddition reaction catalyzed by copper salts was employed for the synthesis of a new series of 1,4-disubstituted triazole compounds containing N-(alkyl)-phthalimides, mono and bis-triazole, in addition to the pyrimidine nucleus: uracil, thymine and fluorouracil. The best yields achieved were 81% for compound (12c), obtained from azide (9a) and alkyne (12a) using acetonitrile (ACN) as solvent and 64% for compound (11g), when we used azide (9b) and the alkyne (11b) in dimethylformamide (DMF) as solvent. In this way, it was possible to synthesize a new series of 1,2,3-triazol-1,4-disubstituted compounds, containing the phthalimide heterocycles and the pyrimidine bases in moderate to good yields. When azide (9a) and ACN were used as solvent it was between 46 to 81%, falling to 11 to 53% when using DMF as solvent. For azide (9b) it was between 14 to 81% with the use of ACN and 20 to 64% with the use of DMF. For azide (9c) ACN was used resulting in yields between 30 and 53%. Thus, 15 unpublished compounds were prepared and sent for antiviral activity study.

COMMITTEE MEMBERS:
Interno - CELSO DE AMORIM CAMARA
Interno - JOAO RUFINO DE FREITAS FILHO
Interno - RONALDO NASCIMENTO DE OLIVEIRA
Externo à Instituição - DJALMA MENEZES DE OLIVEIRA
Externa à Instituição - BRUNA MARTINS GUIMARÃES - UFRPE
Externo à Instituição - LINDOMAR JOSE PENA