Facile one-pot synthesis of novel 1,2,4-Triazin-5-one from intramolecular cyclization

Facile one-pot synthesis of novel 1,2,4-Triazin-5-one from intramolecular cyclization

Rosa, Fernanda A.; Gonçalves, Davana S.; Silva, Michael J. V. da; Tozatti, Camila S. S.; Gauze, Gisele F.

Abstract:

The triazinones are integral part of class bioactive in the heterocyclic compounds. In particular the 1,2,4- Triazin-5-ones are very important in class of these compounds and have attracted particular attention in the pharmaceutical and agrochemical industries, as have exhibited potential activity antitumor, anticancer, antiulcer, and anti-inflammatory effects, activity as herbicides, desiccants, defoliants, plant growth regulators and insecticides. Numerous methods for the synthesis of these compounds have been published, among them, there are condensation reactions of hydrazide and hydrazones with primary amines or acetals derivatives and cyclization obtained by treatment thermal and in the presence of acid. In this work, we attempted to synthesis 1,2,4- triazin- 5-ones through a new method using condensations in the 2-hydrazonopropanehydrazide (1) with N,N-Dimethylformamide dimethyl acetal (DMFDMA) and intramolecular cyclization by acid catalyzed.

The triazinones are integral part of class bioactive in the heterocyclic compounds. In particular the 1,2,4- Triazin-5-ones are very important in class of these compounds and have attracted particular attention in the pharmaceutical and agrochemical industries, as have exhibited potential activity antitumor, anticancer, antiulcer, and anti-inflammatory effects, activity as herbicides, desiccants, defoliants, plant growth regulators and insecticides. Numerous methods for the synthesis of these compounds have been published, among them, there are condensation reactions of hydrazide and hydrazones with primary amines or acetals derivatives and cyclization obtained by treatment thermal and in the presence of acid. In this work, we attempted to synthesis 1,2,4- triazin- 5-ones through a new method using condensations in the 2-hydrazonopropanehydrazide (1) with N,N-Dimethylformamide dimethyl acetal (DMFDMA) and intramolecular cyclization by acid catalyzed.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201391017547

Referências bibliográficas

• [1] KRZYSZTOF SZTANKE, K. P. M. S. M. K.-S. A. E. K. I. D. Bioorganic And Medicinal Chemistry Letters, 19, 2009. 5095–5100.
• [2] RUI-YANG YANG, A. P. K. Tetrahedron Letters, 42, 2001. 4433–4435.
• [3] V. V. ALEKSEYEV, A. G. S. S. I. Y. Chemistry of Heterocyclic Compounds, 48, n. 3, 2012. 506-511.
• [4] V. L. RUSINOV, E. N. U. O. N. C. V. N. C. Russian Chemical Bulletin, 57, n. 5, 2008. 985-1014.
• [5] AHMAD SAMI SHAWALI, S. M. S. Current Organic Chemistry, 11, n. 9, 2007. 773-799.
• [6] DEREK H. R. BARTON, J. C. J. W. L. T. S. Tetrahedron, 52, n. 47, 1996. 14673-1468.
• [7] YASSIN, F. A. Journal of Microbiology and Antimicrobials, 2, n. 7,

Como citar:

Rosa, Fernanda A.; Gonçalves, Davana S.; Silva, Michael J. V. da; Tozatti, Camila S. S.; Gauze, Gisele F.; "Facile one-pot synthesis of novel 1,2,4-Triazin-5-one from intramolecular cyclization", p-67-67. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391017547