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

Authors

  • Александр В. Сафрыгин Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Михаил А. Барабанов Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000
  • Роман А. Иргашев Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000 I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620990
  • Вячеслав Я. Сосновских Institute of Natural Sciences, Ural Federal University named after the First President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000

DOI:

https://doi.org/10.1007/2646

Keywords:

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

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

Author Biography

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

Зав. кафедрой органической химии Института естественных наук Уральского федерального университета

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Published

2015-10-07

Issue

Vol. 51 No. 9 (2015)

Section

Original Papers