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Oxidative halogenation of 6-methyluracil

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Science Center, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa, 450054, Russia

    V. G. Kasradze, I. B. Ignatyeva, R. A. Khusnutdinov & M. S. Yunusov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    K. Yu. Suponitskii & M. Yu. Antipin

Authors
  1. V. G. Kasradze
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  2. I. B. Ignatyeva
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  3. R. A. Khusnutdinov
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  4. K. Yu. Suponitskii
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  5. M. Yu. Antipin
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  6. M. S. Yunusov
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Correspondence to V. G. Kasradze.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1095-1106, July, 2012.

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Kasradze, V.G., Ignatyeva, I.B., Khusnutdinov, R.A. et al. Oxidative halogenation of 6-methyluracil. Chem Heterocycl Comp 48, 1018–1027 (2012). https://doi.org/10.1007/s10593-012-1094-z

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  • DOI: https://doi.org/10.1007/s10593-012-1094-z

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