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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 (free Supporting Information)


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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



Key Words

pyrazoles


ID: J42-Y2017