Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1 H)-one Derivatives

Vladislav Yu Shuvalov; Sergei А Chernenko; Anton L Shatsauskas; Anna L Samsonenko; Maksim V Dmitriev; Alexander S Fisyuk

doi:10.1007/s10593-021-02980-w

Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1 H)-one Derivatives

Chem Heterocycl Compd (N Y). 2021;57(7-8):764-771. doi: 10.1007/s10593-021-02980-w. Epub 2021 Sep 7.

Authors

Vladislav Yu Shuvalov¹, Sergei А Chernenko¹, Anton L Shatsauskas¹, Anna L Samsonenko², Maksim V Dmitriev³, Alexander S Fisyuk^{1

2}

Affiliations

¹ Omsk State Technical University, 11 Mira Ave, Omsk, 644050 Russia.
² Dostoevsky Omsk State University, 55a Mira Ave, Omsk, 644077 Russia.
³ Perm State University, 15 Bukireva St, Perm, 614990 Russia.

Abstract

The reaction of 4-arylidene-2-phenyloxazol-5(4H)-ones with enamines of ethyl acetoacetate gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,4,5,6-tetrahydropyridine-3-carboxylic acid esters, which, when heated with phosphorus oxychloride, were converted into esters of 7-aryl-5-methyl-2-phenyloxazolo[5,4-b]pyridine-6-carboxylic acids. Alkaline hydrolysis of these compounds gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,6-dihydropyridine-3-carboxylic acid esters.

Supplementary information: The online version contains supplementary material available at 10.1007/s10593-021-02980-w.

Keywords: 3-amino-4-arylpyridin-2(1H)-ones; alkaline hydrolysis; azlactones; oxazolo[5,4-b]pyridines; oxidation.