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Synthesis and some chemical properties of 2-cyano-4-pyrone

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Chemistry of Heterocyclic Compounds Aims and scope

2-Cyano-4-pyrone obtained from comanic acid ethyl ester reacts with amines and hydrazines with the opening of the pyrone ring and substitution of the cyano group to form carbamoylated aminoenones (yields 62–87%) and pyrazolylacetic acid hydrazides. The reactions of 2-cyano-4-pyrone with hydroxylamine or sodium azide involve exclusively the cyano group, which makes it possible to obtain 2-heteroaryl-4-pyrones and 2-heteroaryl-4-hydroxypyridines.

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This work was supported by the Russian Science Foundation (grant 18-13-00186).

Elemental analysis was performed and 1H, 13C NMR spectra were recorded on equipment of the Center for collective use “Spectroscopy and analysis of organic compounds” of the Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences and “Laboratory of comprehensive examination and expert evaluation of organic materials” of Ural Federal University.

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave, Yekaterinburg, 620000, Russia

    Dmitrii L. Obydennov, Aleksandra I. Suslova & Vyacheslav Ya. Sosnovskikh

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  1. Dmitrii L. Obydennov
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  2. Aleksandra I. Suslova
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  3. Vyacheslav Ya. Sosnovskikh
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Correspondence to Dmitrii L. Obydennov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(2), 173–179

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Obydennov, D.L., Suslova, A.I. & Sosnovskikh, V.Y. Synthesis and some chemical properties of 2-cyano-4-pyrone. Chem Heterocycl Comp 56, 173–179 (2020). https://doi.org/10.1007/s10593-020-02642-3

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