Synthesis 2020; 52(02): 227-238
DOI: 10.1055/s-0039-1690231
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1Н)-ones

Anton L. Shatsauskas
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
,
Anton A. Abramov
b   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation
,
Sergey A. Chernenko
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
,
Anastasia S. Kostyuchenko
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
b   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation
,
a   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
› Author Affiliations
This work was supported by the Russian Science Foundation (grant No. 19-13-00273).
Further Information

Publication History

Received: 27 August 2019

Accepted after revision: 12 October 2019

Publication Date:
31 October 2019 (online)


Abstract

A method has been developed for the preparation of oxazolo-[5,4-b]pyridin-2(1H)-ones based on the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides. Hydrolysis of oxazolo[5,4-b]pyridin-2(1H)-ones and the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides yielded 3-aminopyridin-2(1H)-ones, including 4-aryl substituted derivatives in the series, for which effective phosphors with a quantum yield of up to 0.78 were detected. Photophysical properties of 3-aminopyridin-2(1H)-ones were studied by UV and luminescence spectroscopy methods, and the relationship between their structure and photophysical properties was revealed.

Supporting Information