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Synthesis of 5-Chloro-3-styryl-1H-pyrazoles Based on 2,2-Dichlorovinyl Ketones

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Abstract

The condensation of 4,4-dichlorobut-3-en-2-one with aromatic aldehydes in the presence of a cata­lytic amount of sulfuric acid afforded 1,1-dichloro-5-(4-R-phenyl)penta-1,4-dien-3-ones which reacted with substituted hydrazines under mild conditions in chemo- and regioselective fashion to give 3-[(E)-2-arylethenyl]-5-chloro-1-methyl-1H-pyrazoles in up to 81% yield. The reaction of 4-bromo-1,1-dichloro-5-(4-methoxy­phenyl)­penta-1,4-dien-3-one with N,N-dimethylhydrazine produced 3-[1-bromo-2-(4-methoxyphenyl)­ethenyl]-5-chloro-1-methyl-1H-pyrazole which was converted to 5-chloro-3-[(4-methoxyphenyl)­ethynyl]-1-methyl-1H-pyrazole in 69% yield on heating in DMSO in the presence of KF at 120°C. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectra and elemental analyses.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the facilities of the Baikal joint analytical center at the Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences.

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    V. A. Kobelevskaya, S. V. Zinchenko & A. V. Popov

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  1. V. A. Kobelevskaya
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  2. S. V. Zinchenko
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  3. A. V. Popov
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Correspondence to V. A. Kobelevskaya.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 6, pp. 772–780 https://doi.org/10.31857/S0514749223060058.

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Kobelevskaya, V.A., Zinchenko, S.V. & Popov, A.V. Synthesis of 5-Chloro-3-styryl-1H-pyrazoles Based on 2,2-Dichlorovinyl Ketones. Russ J Org Chem 59, 1000–1007 (2023). https://doi.org/10.1134/S1070428023060052

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