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Synthesis of 4-Acyl-3-Aminofurazans from 3,4-Diacylfuroxans

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Chemistry of Heterocyclic Compounds Aims and scope

It was shown that 3,4-diaroylfuroxans are transformed into the corresponding 3-amino-4-aroyl-furazans by heating in aqueous ammonia. The developed one-pot methodology for the synthesis of 3-amino-4-aroylfurazans involved the interaction of the corresponding acetophenones with nitric acid followed by treatment of the in situ formed furoxans with ammonia at elevated temperature. The structures of the obtained furazans were confirmed by IR, as well as by 1H and 13C NMR spectroscopy, and X-ray structural analysis was performed for 3-amino-4-(4-methoxybenzoyl)furazan.

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A. B. Sheremetev and N. V. Palysaeva would like to express their gratitude to the Russian Science Foundation for financial support towards their experimental research and the study of spectral characteristics (SFR, project 14-13-01153).

K. Yu. Suponitsky would like to acknowledge the financial support from the Russian Science Foundation for structural investigations (SFR, project 14-13-00884).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    A. B. Sheremetev, S. G. Zabusov, T. R. Tukhbatshin & N. V. Palysaeva

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    K. Yu. Suponitsky

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  1. A. B. Sheremetev
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  2. S. G. Zabusov
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  3. T. R. Tukhbatshin
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Correspondence to A. B. Sheremetev.

Additional information

Supplementary information files containing 1Н, 13С, 15N, and 19F NMR spectra of compound 2с are available at http://hgs.osi.lv.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1250-1262, August, 2014.

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Sheremetev, A.B., Zabusov, S.G., Tukhbatshin, T.R. et al. Synthesis of 4-Acyl-3-Aminofurazans from 3,4-Diacylfuroxans. Chem Heterocycl Comp 50, 1154–1165 (2014). https://doi.org/10.1007/s10593-014-1576-2

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