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Comparison of Conventional and Microwave Synthesis of Phenyl-1H-pyrazoles and Phenyl-1H-pyrazoles-4-carboxylic Acid Derivatives

Author(s):

Antônio S. Machado, Flávio S. de Carvalho, Rayssa B.P. Mouraa, Lorrayne S. Chaves, Luciano M. Lião, Germán Sanz, Boniek G. Vaz, Marcella F. Rodrigues, Wanderson Romão, Ricardo Menegatti and Gloria N.S. Silva*   Pages 1 - 10 ( 10 )

Abstract:


Background: Privileged scaffolds are of high importance for molecules containing the pyrazole subunit due to their broad spectrum of pharmacological activities. For this reason, a method that is more efficient needs to be developed for the preparation of pyrazole derivatives.

Objective: The purpose of this study was the optimisation of the conventional synthesis of the pyrazole ring and the oxidation of phenyl-1H-pyrazole-4-carbaldehyde to phenyl-1H-pyrazole-4-carboxylic acid through Microwave- Assisted Organic Synthesis (MAOS).

Methods: We performed a comparison between conventional synthesis and conventional synthesis with microwave heating using the synthesis method of pyrazole ring described by Finar and Godfrey and for the oxidation of phenyl-1H-pyrazole-4-carbaldehyde, the method described by Shriner and Kleiderer was used.

Results: MAOS reduces the reaction time to obtain all compounds compared to conventional heating. At a temperature of 60°C, 5 minutes of reaction time, and power of 50 W, the yield of phenyl-1H-pyrazoles (3a-m) compounds was in the range of 91 - 98% using MAOS, which is better than conventional heating (72 - 90%, 75ºC, 2 hours). An improvement in the yield for the oxidation reaction was also achieved with MAOS. The compounds (5a-m) were obtained with yields ranging from 62 - 92% (80ºC, 2 minutes, 150 W), while the yields with conventional heating were in the range of 48 - 85% (80ºC, 1 hour). The 26 compounds were achieved through an easy work-up procedure with no chromatographic separation. The pure products were characterised by the spectral data obtained from IR, MS, 1H and 13C NMR or HSQC/HMBC techniques.

Conclusion: The advantages of MAOS include short reaction time and increased yield, due to which it is an attractive option for pyrazole compounds synthesis.

Keywords:

Pyrazole, heterocycle, privileged scaffolds, synthesis, conventional heating, microwave irradiation.

Affiliation:

Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO, Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO, Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO, Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO, Laboratory of Nuclear Magnetic Resonance, Chemistry Institute, Federal University of Goiás, Goiânia, GO, Laboratory of Chromatography and Mass Spectrometry (LaCEM), Chemistry Institute, Federal University of Goiás, Goiânia, GO, Laboratory of Chromatography and Mass Spectrometry (LaCEM), Chemistry Institute, Federal University of Goiás, Goiânia, GO, Laboratory of Chromatography and Mass Spectrometry (LaCEM), Chemistry Institute, Federal University of Goiás, Goiânia, GO, Federal Institute of Espírito Santo (IFES), Ministro Salgado Filho Avenue, Soteco, Vila Velha, ES, 29106-010, Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO, Laboratory of Medicinal Pharmaceutical Chemistry, College of Pharmacy, Federal University of Goiás, Goiânia, GO



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