Facile synthesis of 6-organyl-4-(trifluoromethyl)pyridin-2(1 H)-ones and their polyfluoroalkyl-containing analogs

S O Kushch; M V Goryaeva; Ya V Burgart; G A Triandafilova; K O Malysheva; O P Krasnykh; N A Gerasimova; N P Evstigneeva; V I Saloutin

doi:10.1007/s11172-022-3579-y

Facile synthesis of 6-organyl-4-(trifluoromethyl)pyridin-2(1 H)-ones and their polyfluoroalkyl-containing analogs

Russ Chem Bull. 2022;71(8):1687-1700. doi: 10.1007/s11172-022-3579-y. Epub 2022 Sep 23.

Authors

S O Kushch¹, M V Goryaeva¹, Ya V Burgart¹, G A Triandafilova², K O Malysheva², O P Krasnykh², N A Gerasimova³, N P Evstigneeva³, V I Saloutin¹

Affiliations

¹ I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108 Yekaterinburg, Russian Federation.
² Perm National Research Polytechnic University, 29 Komsomolskii prosp., 614990 Perm, Russian Federation.
³ Ural Research Institute of Dermatovenereology and Immunopathology, 8 ul. Shcherbakova, 620076 Yekaterinburg, Russian Federation.

Abstract

The three-component cyclization of 3-polyfluoroalkyl-3-oxopropanoates and methyl ketones with ammonium acetate affords 6-organyl-4-(polyfluoroalkyl)pyridin-2(1H)-ones (organyl is alkyl, aryl, or hetaryl). The synthesized pyridones were evaluated for antifungal, antibacterial, and analgesic activity.

Keywords: 3-polyfluoroalkyl-3-oxopropanoates; 4-(trifluoromethyl)pyridin-2-ones; ammonium acetate; ethyl trifluoroacetoacetate; methyl ketones; three-component reaction.