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Reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with guanidine. Synthesis of new 1,3,5-triazine derivatives

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Abstract

2-(2-Furyl)- and 2-(2-thienyl)-5-alkyl-4-hydroxy-6H-1,3-oxazin-6-ones react with guanidine in methanol in the presence of an equimolar amount of sodium methoxide to give previously unknown sodium 4-amino-6-hetaryl-1,3,5-triazin-2-ylacetates. The reactions of 2-(2-furyl)- and 2-(2-thienyl)-5-phenyl-4-hydroxy-6H-1,3-oxazin-6-ones with guanidine under analogous conditions are accompanied by decarboxylation, yielding 4-benzyl-6-hetaryl-1,3,5-triazin-2-amines. The corresponding decarboxylation products are also obtained by treatment of sodium 2-(4-amino-6-hetaryl-1,3,5-triazin-2-yl)propionates with aqueous HCl.

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Authors and Affiliations

  1. St. Petersburg State Chemical-Pharmaceutical Academy, ul. Prof. Popova 14A, St. Petersburg, 197376, Russia

    N. M. Chernov, I. P. Yakovlev, V. E. Zakhs, T. L. Semakova & G. V. Ksenofontova

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  1. N. M. Chernov
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  2. I. P. Yakovlev
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  3. V. E. Zakhs
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  4. T. L. Semakova
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  5. G. V. Ksenofontova
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Correspondence to N. M. Chernov.

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Original Russian Text © N.M. Chernov, I.P. Yakovlev, V.E. Zakhs, T.L. Semakova, G.V. Ksenofontova, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 11, pp. 1837–1841.

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Chernov, N.M., Yakovlev, I.P., Zakhs, V.E. et al. Reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with guanidine. Synthesis of new 1,3,5-triazine derivatives. Russ J Gen Chem 85, 2578–2582 (2015). https://doi.org/10.1134/S1070363215110122

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  • DOI: https://doi.org/10.1134/S1070363215110122

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