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Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with O-nucleophiles

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Abstract

Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with oxygen-centered nucleophiles were studied. 2-Alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones reacted with water and alcohols to give the corresponding alkyl 3-amino-3-oxopropanoates as a result of opening of the oxazine ring at the C6-O bond, whereas their 2-alkylsulfanyl analogs turned out to be stable toward O-nucleophiles. The different reactivities of the title compounds were interpreted in terms of quantum-chemical calculations of their electronic structure.

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Authors and Affiliations

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

    B. Yu. Lalaev, I. P. Yakovlev, N. N. Kuz’mich, G. V. Ksenofontova & V. E. Zakhs

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  1. B. Yu. Lalaev
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  2. I. P. Yakovlev
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  3. N. N. Kuz’mich
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  4. G. V. Ksenofontova
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  5. V. E. Zakhs
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Corresponding author

Correspondence to B. Yu. Lalaev.

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Original Russian Text © B.Yu. Lalaev, I.P. Yakovlev, N.N. Kuz’mich, G.V. Ksenofontova, V.E. Zakhs, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 10, pp. 1734–1738.

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Lalaev, B.Y., Yakovlev, I.P., Kuz’mich, N.N. et al. Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with O-nucleophiles. Russ J Gen Chem 80, 2043–2047 (2010). https://doi.org/10.1134/S1070363210100269

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  • DOI: https://doi.org/10.1134/S1070363210100269

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