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Reaction of 3-Hydrazinylquinoxaline-2(1H)-one with 2-Hydroxyimino-1,3-dicarbonyl Compounds

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Abstract

3-Hydrazinylquinoxalin-2(1H)-one reacts with ethyl 2-hydroxyimino-3-oxobutanoate or 1-Ar-2-(hydroxyimino)-butane-1,3-diones (Ar = Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, naphthalen-1-yl) in acetic acid to form a mixture of the E- and Z-hydrazones in excellent yields. The reaction of 3-hydrazinylquinoxalin-2(1H)-one with 1-(pyridin-4-yl)-2-(hydroxyimino)butane-1,3-dione gave 3-[5-hydroxy-4-(hydroxyimino)-3-methyl-5-(pyridin-4-yl)-4,5-dihydro-1H-pyrazol-1-yl]quinoxalin-2(1H)-one. The reaction with 2-hydroxyimino-3-oxobutanal in ethanol leads to 3-{2-[2-(hydroxyimino)-3-oxobutylidene]hydrazinyl}quinoxalin-2(1H)-one. The structures of the synthesized compounds were determined by UV–Vis, IR, and 1H and 13C NMR spectroscopy, chromatography–mass spectrometry, and elemental analysis. Proton signals were assigned using 2D homo- (1H–1H COSY) and heteronuclear (1H–13C HSQC, 1H–13C HMBC, 1H–15N HMBC) experiments.

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ACKNOWLEDGMENTS

The NMR spectra were registered for the Institute of Chemistry and Chemical Technology, Siberian Branch, Russian Academy of Sciences, on 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, E. S. Semichenko & 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. E. S. Semichenko
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  3. A. A. Kondrasenko
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  4. 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. 1214–1223 https://doi.org/10.31857/S0514749222110106.

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Bobrov, P.S., Semichenko, E.S., Kondrasenko, A.A. et al. Reaction of 3-Hydrazinylquinoxaline-2(1H)-one with 2-Hydroxyimino-1,3-dicarbonyl Compounds. Russ J Org Chem 58, 1628–1636 (2022). https://doi.org/10.1134/S1070428022110100

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