Theoretical study of the regiospecific synthesis of pyrazole-5- carboxylate from unsymmetrical enaminodiketones

Theoretical study of the regiospecific synthesis of pyrazole-5- carboxylate from unsymmetrical enaminodiketones

Rozada, Thiago C.; Silva, Michael J. V. da; Pontes, Rodrigo M.; Basso, Ernani A.; Rosa, Fernanda A.

Abstract:

The synthesis of pyrazoles has been the subject of consistent interest because of the wide applications for such heterocycles. Nevertheless the synthesis of such compounds with unsymmetrical 1,3-dicarbonyl substrates often produces a regioisomeric mixture of pyrazoles with generally poor selectivity. However, Rosa and co-workers reported the regiospecific synthesis of pyrazole-5-carboxylates from unsymmetrical enaminodiketones. Thus, considering the application of pyrazoles and the regiospecificity of the reactions presented by Rosa, we conducted a detailed theoretical investigation of the structure of the reagents, products and possible transition states in the reactions (Figure 1).

The synthesis of pyrazoles has been the subject of consistent interest because of the wide applications for such heterocycles. Nevertheless the synthesis of such compounds with unsymmetrical 1,3-dicarbonyl substrates often produces a regioisomeric mixture of pyrazoles with generally poor selectivity. However, Rosa and co-workers reported the regiospecific synthesis of pyrazole-5-carboxylates from unsymmetrical enaminodiketones. Thus, considering the application of pyrazoles and the regiospecificity of the reactions presented by Rosa, we conducted a detailed theoretical investigation of the structure of the reagents, products and possible transition states in the reactions (Figure 1).

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013104184411

Referências bibliográficas

• [1] 1 Katritzky, A. R.; Wang, M.; Zhang, S.; Voronkov, M. V. J. Org. Chem. 2001, 66, 6787.
• [2] 2 Rosa, F. A.; Machado, P.; Vargas, P. S.; Bonacorso, H. G., Zanatta, N.; Martins, M. A. P. Synlett 2008, 11, 1673.

Como citar:

Rozada, Thiago C.; Silva, Michael J. V. da; Pontes, Rodrigo M.; Basso, Ernani A.; Rosa, Fernanda A.; "Theoretical study of the regiospecific synthesis of pyrazole-5- carboxylate from unsymmetrical enaminodiketones", p-139-139. 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_2013104184411