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Synthesis and reactivity of 4-hydroxy-5-methyl-2-(2-oxo-2H-chromen-3-yl)-6H-1,3-oxazin-6-ones

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Abstract

4-Hydroxy-6H-1,3-oxazin-6-ones with a coumarin fragment in position 2 of the oxazine ring were synthesized. Their hydrolysis, alcoholysis, and hydrazinolysis afforded a number of new coumarin derivatives containing malonamic acid and 1,2,4-triazole residues. The low stability of the title compounds toward oxygencentered nucleophiles was interpreted by quantum chemical calculations.

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Authors and Affiliations

  1. St. Petersburg State Chemical Pharmaceutical Academy, ul. Professora Popova 14/A, St. Petersburg, 197376, Russia

    N. M. Chernov, P. V. Filippova, I. P. Yakovlev & V. E. Zakhs

  2. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Belyakov

Authors
  1. N. M. Chernov
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  2. P. V. Filippova
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  3. I. P. Yakovlev
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  4. V. E. Zakhs
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  5. A. V. Belyakov
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Corresponding author

Correspondence to N. M. Chernov.

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Original Russian Text © N.M. Chernov, P.V. Filippova, I.P. Yakovlev, V.E. Zakhs, A.V. Belyakov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 6, pp. 962–969.

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Chernov, N.M., Filippova, P.V., Yakovlev, I.P. et al. Synthesis and reactivity of 4-hydroxy-5-methyl-2-(2-oxo-2H-chromen-3-yl)-6H-1,3-oxazin-6-ones. Russ J Gen Chem 86, 1292–1299 (2016). https://doi.org/10.1134/S1070363216060128

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  • DOI: https://doi.org/10.1134/S1070363216060128

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