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A versatile solvent-free synthesis of novel pyrazolone-1,3-dithiolan and pyrazolone-1,3-dithiole hybrids

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Abstract

In this study, an efficient one-pot, solvent-free synthesis of pyrazolone-1,3-dithiolan and pyrazolone-1,3-dithiole hybrids from the reaction between in situ generated pyrazolones and propargyl bromide in the presence of carbon disulfide is reported. This reaction was carried out in the presence of triethylamine at room temperature, and new pyrazolone-1,3-dithiolan and pyrazolone-1,3-dithiole hybrids were formed in good to high yields. In the 1H NMR spectra of synthesized 1,3-dithiole hybrid molecules, the signal of olefinic hydrogen appeared at about 7.07–7.41 ppm in DMSO-d6. The values of these chemical shifts indicate that both linked pyrazole and dithiole rings in the dithiole-pyarzolone hybrid molecules have aromatic properties.

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1H NMR, 13C NMR, and mass spectra of all new compounds associated with this article can be found in the online version.

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Acknowledgements

Financial support of this research by the University of Mohaghegh Ardabili, Iran, is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Applied Chemistry, University of Mohaghegh Ardabili, P.O. Box 56199-11367, Ardabil, Iran

    Jaber Salehzadeh & Farough Nasiri

Authors
  1. Jaber Salehzadeh
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  2. Farough Nasiri
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Contributions

JS: Doing entire experimental work, Writing—original draft, Writing-review & editing. FN: Project administration, Supervision, Writing—review & editing.

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Correspondence to Farough Nasiri.

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Salehzadeh, J., Nasiri, F. A versatile solvent-free synthesis of novel pyrazolone-1,3-dithiolan and pyrazolone-1,3-dithiole hybrids. Res Chem Intermed 49, 4621–4637 (2023). https://doi.org/10.1007/s11164-023-05087-3

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