DESIGN, SYNTHESIS, AND STRUCTURE OF ALKYL 1<i>H</i>-PYRAZOLECARBOXYLATES FROM A RASPBERRY KETONE METHYL ETHER

Authors

  • Taís B. Goulart School of Chemistry and Food, Federal University of Rio Grande, Rio Grande 96203-900, RS, Brazil
  • Adriana M. Neves School of Chemistry and Food, Federal University of Rio Grande, Rio Grande 96203-900, RS, Brazil
  • Mayara S. P. Soares Laboratory of Biomarkers, Center for Chemical, Pharmaceutical and Food Sciences, Federal University of Pelotas, Capão do Leão 96010-900, RS, Brazil
  • Francieli M. Stefanello Laboratory of Biomarkers, Center for Chemical, Pharmaceutical and Food Sciences, Federal University of Pelotas, Capão do Leão 96010-900, RS, Brazil
  • Patrick T. Campos Laboratory of Synthetic, Structural and Computational Organic Chemistry, Sulriograndense Federal Institute (IFSul), Pelotas 96015-360, RS, Brazi
  • Sidnei Moura Biotechnology Institute, University of Caxias do Sul, Caxias do Sul 95070-560, RS, Brazil
  • Roberta Cargnelutti Chemistry Department, Federal University of Santa Maria, Santa Maria 97105-900, RS, Brazil
  • Alex F. C. Flores School of Chemistry and Food, Federal University of Rio Grande, Rio Grande 96203-900, RS, Brazil

DOI:

https://doi.org/10.1007/5863

Keywords:

4-alkoxy-1, 1, 1-trichloroalk-3-en-2-ones, 1H-pyrazolecarboxylates, raspberry ketone, antioxidants, microwave irradiation.

Abstract

This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1H-pyrazole-3-carboxylates via cyclocondensation of 1,1,1-trichloro-
4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et, n-Pr, i-Pr, i-Bu, i-Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system.

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Published

2020-11-05

Issue

Vol. 56 No. 10 (2020)

Section

Original Papers