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Chemical Properties of 6-Methyluracil-5-carbaldehyde Oxime

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Abstract

Oxidative chlorination of 6-methyluracil-5-carbaldehyde oxime in a two-phase system gave 7V-hydroxy-6-methyluracil-5-carboximidoyl chloride, and its bromination afforded ipso-substitution products, 5-bromo-6-methyluracil and 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil. The reaction of the title compound with acetic anhydride led to the formation of 6-methyluracil-5-carbonitrile or O-acetyl derivative, depending on the temperature. 7V-Hydroxy-6-methyluracyl-5-carboximidoyl chloride reacted with acetic acid at 100°C or with potassium iodide in boiling acetone to produce uracil-5-hydroxamic acid which was converted with high yields into the corresponding methyl ester and hydroximic acid amide. Quaternary ammonium salts were obtained by reactions of N-hydroxy-6-methyluracil-5-carboximidoyl chloride with pyridine and 1-methyl-1H-imidazole.

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Acknowledgments

The spectral studies and DFT calculations were performed using the facilities of the “Chemistry” joint center, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Funding

This study was performed in the framework of state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. AAAA-A17-117011910025-6) and under financial support by the Russian Foundation for Basic Research (project no. 18-53-41004 Uzb_t).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia

    I. B. Chernikova, S. L. Khursan, L. V. Spirikhin & M. S. Yunusov

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  1. I. B. Chernikova
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  2. S. L. Khursan
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  3. L. V. Spirikhin
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  4. M. S. Yunusov
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Correspondence to I. B. Chernikova.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 13672–1375.

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Chernikova, I.B., Khursan, S.L., Spirikhin, L.V. et al. Chemical Properties of 6-Methyluracil-5-carbaldehyde Oxime. Russ J Org Chem 55, 1287–1294 (2019). https://doi.org/10.1134/S1070428019090045

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