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Synthesis of N-Benzothiazolyl-4-nitrosopyrazoles

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Abstract

The cyclocondensation of 2-hydrazinylbenzothiazole with 2-(hydroxyimino)-1,3-diketones, leading to previously unknown 3-R2-5-R1-1-(benzothiazol-2-yl)-4-nitrosopyrazoles (R1 = Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, Me; R2 = Ph, Me), is studied for the first time. The cyclocondensation of 2-hydrazinylbenzothiazole with 1-aryl-2-(hydroxyimino)butane-1,3-diones gives only one of the two possible regioisomers. The synthesized benzothiazolylnitrosopyrazoles were characterized by UV−Vis, IR, and 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis.

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ACKNOWLEDGMENTS

The NMR spectra were registered for the Institute of Chemistry and Chemical Technology, Siberian Branch, Russian Academy of Sciences, at the equipment of the Krasnoyarsk Regional Center for Collective Use, Krasnoyarsk Scientific Center of the Siberian Branch of the Russian Academy of Sciences Federal Research Center.

Funding

Registration of the NMR spectra was funded from the state budget (project no. 0287-2021-0012).

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Authors and Affiliations

  1. Reshetnev Siberian State University of Science and Technology, 660037, Krasnoyarsk, Russia

    P. S. Bobrov & G. A. Suboch

  2. Institute of Chemistry and Chemical Technology, SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”, 660036, Krasnoyarsk, Russia

    A. A. Kondrasenko

Authors
  1. P. S. Bobrov
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  2. A. A. Kondrasenko
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  3. G. A. Suboch
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Correspondence to P. S. Bobrov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1224–1228 https://doi.org/10.31857/S0514749222110118.

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Bobrov, P.S., Kondrasenko, A.A. & Suboch, G.A. Synthesis of N-Benzothiazolyl-4-nitrosopyrazoles. Russ J Org Chem 58, 1637–1640 (2022). https://doi.org/10.1134/S1070428022110112

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  • DOI: https://doi.org/10.1134/S1070428022110112

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