NOVEL APPROACH TO THE SYNTHESIS OF 3-AMINO-4-ARYLPYRIDIN-2(1<i>H</i>)-ONE DERIVATIVES

Authors

  • Владислав Ю. Шувалов Omsk State Technical University, 11 Mira Ave., Omsk 644050
  • Сергей А. Черненко Omsk State Technical University, 11 Mira Ave., Omsk 644050
  • Антон Л. Шацаускас Omsk State Technical University, 11 Mira Ave., Omsk 644050
  • Анна Л. Самсоненко Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077
  • Максим В. Дмитриев Perm State University, 15 Bukireva St., Perm 614990
  • Александр С. Фисюк Omsk State Technical University, 11 Mira Ave., Omsk 644050 Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077

DOI:

https://doi.org/10.1007/6361

Keywords:

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

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.

Authors: Vladislav Yu. Shuvalov, Sergei А. Chernenko, Anton L. Shatsauskas,
Anna L. Samsonenko, Maksim V. Dmitriev, Alexander S. Fisyuk*

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Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers