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Synthesis and reactivity of 8-aza-5,7-dimethyl-2-trifluoroacetylchromone

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Chemistry of Heterocyclic Compounds Aims and scope

Claisen condensation of 3-acetyl-4,6-dimethyl-2-pyridone with methyl 2-methoxytetrafluoropropionate in the presence of LiH in refluxing dioxane gave the corresponding 1,3-diketone, further converted by treatment with conc. H2SO4 to 5,7-dimethyl-2-(1-methoxytetrafluoroethyl)-8-azachromone and 5,7-dimethyl-2-trifluoroacetyl-8-azachromone, which was isolated as hydrate. The first of these azachromones reacted with dinucleophiles at the С-2 atom and the pyrone carbonyl group, while the second reacted at the С-2 atom and trifluoroacetyl group. Based on these compounds, we obtained new trifluoromethylated heterocyclic systems containing a 2-pyridone ring, as well as (8-azachromon-2-yl)(indol-3-yl)carbinols.

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Authors and Affiliations

  1. Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Alexander V. Safrygin, Mikhail A. Barabanov, Roman A. Irgashev & Vyacheslav Ya. Sosnovskikh

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Roman A. Irgashev

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  1. Alexander V. Safrygin
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  2. Mikhail A. Barabanov
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  3. Roman A. Irgashev
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  4. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vyacheslav Ya. Sosnovskikh.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(9), 838–844

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Safrygin, A.V., Barabanov, M.A., Irgashev, R.A. et al. Synthesis and reactivity of 8-aza-5,7-dimethyl-2-trifluoroacetylchromone. Chem Heterocycl Comp 51, 838–844 (2015). https://doi.org/10.1007/s10593-015-1784-4

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