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SYNTHESIS AND REACTIVITY OF 8-AZA-5,7-DIMETHYL- 2-TRIFLUOROACETYLCHROMONE

Александр В. Сафрыгин, Михаил А. Барабанов, Роман А. Иргашев, Вячеслав Я. Сосновских
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Abstract


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.

How to Cite
Safrygin, A. V.; Barabanov, M. A.; Irgashev, R. A.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 838. [Khim. Geterotsikl. Soedin. 2015, 51, 838.]

For this article in the English edition see DOI 10.1007/s10593-015-1784-4


Keywords


8-azachromones; bis-hetarylcarbinols; 1,2-diamines; indoles; quinoxalines; trifluoromethylated heterocycles

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