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One-pot solvent-free synthesis of 1,3,5-trisubstituted 1H-pyrazoles catalyzed by H3[PW12O40]/SiO2 under microwave irradiation

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Abstract

An efficient synthesis of 1,3,5-trisubstituted 1H-pyrazoles was developed. 1,3,5-Trisubstituted-1H-pyrazoles were synthesized starting from α,β-unsaturated aldehydes/ketones and hydrazine using catalyst H3[PW12O40]/SiO2 under microwave irradiation and solvent-free conditions (74–90%) and were characterized by HR-MS, FT-IR, 1H NMR, and 13C NMR spectroscopy. It was found that silica had a good loading and dispersing effect on phosphotungstic acid and could effectively absorb microwave energy to promote the condensation reaction. The merits of the method included the environmental friendly reaction conditions, simple operation, extensive substrates, good yields, and reuse of the H3[PW12O40]/SiO2. Moreover, the crystal structure of compound 1-(4-chlorophenyl)-5-(2-methoxyphenyl)-3-(4-nitrophenyl)-1H-pyrazole in triclinic P-1 space group was presented.

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Acknowledgements

We are grateful to Mr. Ch. Y. Wang for NMR spectra, Mr. Zh. L. Wei for mass spectra. Financial support from the ‘Science and Technology Research Project of Jilin Institute of Chemical Technology (2018035)’ and ‘Jilin Institute of Chemical Technology Ph.D. Starts Fund Project (2018007)’ is gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemistry and Pharmaceutical Engineering, Jilin Institute Chemical Technology, Jilin, 132022, People’s Republic of China

    Dawei Zhang, Ailing Liu, Wenyu Li & Yuxin Liu

  2. College of Aeronautical Engineering, Jilin Institute Chemical Technology, Jilin, 132022, People’s Republic of China

    Lu Ren

  3. College of Chemistry, Jilin University, Changchun, 130012, People’s Republic of China

    Qiang Gu

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  1. Dawei Zhang
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  2. Lu Ren
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  3. Ailing Liu
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  4. Wenyu Li
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Correspondence to Qiang Gu.

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Zhang, D., Ren, L., Liu, A. et al. One-pot solvent-free synthesis of 1,3,5-trisubstituted 1H-pyrazoles catalyzed by H3[PW12O40]/SiO2 under microwave irradiation. Monatsh Chem 153, 257–266 (2022). https://doi.org/10.1007/s00706-022-02902-2

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  • DOI: https://doi.org/10.1007/s00706-022-02902-2

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