Synthesis of new biheterocyclic 4-(2-(1,3,4-oxadiazol-2- yl)ethyl)-6-(trifluoromethyl)pyrimidines

Synthesis of new biheterocyclic 4-(2-(1,3,4-oxadiazol-2- yl)ethyl)-6-(trifluoromethyl)pyrimidines

Malavolta, Juliana L.; Flores, Alex F. C.; Goularte, Rayane B.; Souto, Alynne A.; Doneda, Morgana

Abstract:

Among the heterocyclic compounds pyrimidines and oxadiazoles stand out because of their biological and medicinal importance. Pyrimidines have been used as antibiotics, antineoplastic, among others. On the other hand, 1,3,4-oxadiazoles have been identified as the main core of many bioactive molecules exercising antiinflamatory, antimicrobial and anticonvulsant activities. In recent years we have focused our interest on methyl 7,7,7-trihalo-4-methoxy-6-oxo-3-heptenoates. These represent significant and versatile halogencontaining building block for the synthesis of heterocyclic systems, which often show high biological activities. In connection with our studies on the synthesis of azole and pyrazine derivatives we were interested in developing general and convenient methods for the synthesis of biheterocyclic systems from methyl 7,7,7-trihalo-4-methoxy-6-oxo-3-heptenoates. Here we report the synthesis of 4-(2-(1,3,4-oxadiazol-2- yl)ethyl)-6-trifluoromethylpyrimidines (6-10) from 3- (6-trifluoromethylpyrimidin-4-yl)propanehydrazide and aromatic aldehydes.

Among the heterocyclic compounds pyrimidines and oxadiazoles stand out because of their biological and medicinal importance. Pyrimidines have been used as antibiotics, antineoplastic, among others. On the other hand, 1,3,4-oxadiazoles have been identified as the main core of many bioactive molecules exercising antiinflamatory, antimicrobial and anticonvulsant activities. In recent years we have focused our interest on methyl 7,7,7-trihalo-4-methoxy-6-oxo-3-heptenoates. These represent significant and versatile halogencontaining building block for the synthesis of heterocyclic systems, which often show high biological activities. In connection with our studies on the synthesis of azole and pyrazine derivatives we were interested in developing general and convenient methods for the synthesis of biheterocyclic systems from methyl 7,7,7-trihalo-4-methoxy-6-oxo-3-heptenoates. Here we report the synthesis of 4-(2-(1,3,4-oxadiazol-2- yl)ethyl)-6-trifluoromethylpyrimidines (6-10) from 3- (6-trifluoromethylpyrimidin-4-yl)propanehydrazide and aromatic aldehydes.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0107-1

Referências bibliográficas

• [1] 1 Katritzky and Rees. Comprehensive Heterocyclic Chemistry, Vol.1-8, 1 Pergamon Press, Oxford, 1st ed.1984, 2nd ed. 1995.
• [2] 2 Jaiprakash, N. S.; Aniruddha, R. C.; Devanand, B. S., Bioorg. Med. Chem. Lett. 2011, 21, 444.
• [3] 3 Flores, A. F. C.; Flores, D. C.; Oliveira, G.; Pizzuti, L.; da Silva, R. M. S.; Martins, M. A. P.; Bonacorso, H. G. J. Braz. Chem. Soc. 2008, 19, 184. Flores, A. F. C.; Pizzuti, L.; Piovesan, L. A.; Flores, D. C.; Malavolta, J. L.; Pereira, C. M. P. Tetrahedron Lett. 2010, 51, 4908.
• [4] 4 Flores, A. F. C.; Pizzuti, L.; Brondani, S.; Rossato, M.; Zanatta, N.; Martins, M. A. P. J. Braz. Chem. Soc. 2007, 18, 1316.

Como citar:

Malavolta, Juliana L.; Flores, Alex F. C.; Goularte, Rayane B.; Souto, Alynne A.; Doneda, Morgana; "Synthesis of new biheterocyclic 4-(2-(1,3,4-oxadiazol-2- yl)ethyl)-6-(trifluoromethyl)pyrimidines", p-107-107. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0107-1