Unconventional Method for Synthesis of 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles

Michael J. V. da Silva, Julia Poletto, Andrey P. Jacomini, Karlos E. Pianoski, Davana S. Gonçalves, Gessica M. Ribeiro, Samara M. de S. Melo, Davi F. Back, Sidnei Moura and Fernanda A. Rosa*

*Departamento de Química, Universidade Estadual de Maringá (UEM), 87030-900 Maringá, PR, Brazil, Email: farosauem.br

M. J. V. da Silva, J. Poletto, A. P. Jacomini, K. E. Pianoski, D. S. Gonçalves, G. M. Ribeiro, S. M. de. S. Melo, D. F. Back, S. Moura, F. A. Rosa, J. Org. Chem., 2017, 82, 12590-12602.

DOI: 10.1021/acs.joc.7b02361

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Abstract

Regiochemical control of the cyclocondensation reaction of β-enamino diketones with arylhydrazines enables one-pot procedures for highly regioselective synthesis of 3,5-disubstituted 4-formyl-N-arylpyrazoles or 3,5-disubstituted 4-hydroxymethyl-N-arylpyrazoles. Structural modifications in the β-enamino diketone system allied to the Lewis acid carbonyl activator BF₃ were strategically employed for this control.

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proposed mechanism

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Key Words

pyrazoles

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ID: J42-Y2017