One-Pot Synthesis of Fluorescent 3-Amino-2-arylquinolin-4(1H)-ones from Isatoic Anhydride and 1-(2-Oxo-2-arylethyl)pyridinium Salts

Sergey A. Kirnosov; Anton L. Shatsauskas; Alina V. Petrova; Tatyana Yu. Zheleznova; Vladislav Yu. Shuvalov; Anastasia S. Kostyuchenko; Alexander S. Fisyuk

doi:10.1055/a-2556-3115

Synthesis, Table of Contents

Synthesis 2025; 57(12): 1955-1964
DOI: 10.1055/a-2556-3115

paper

One-Pot Synthesis of Fluorescent 3-Amino-2-arylquinolin-4(1H)-ones from Isatoic Anhydride and 1-(2-Oxo-2-arylethyl)pyridinium Salts

Authors

Sergey A. Kirnosov

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation
Anton L. Shatsauskas ∗

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation
Alina V. Petrova

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation
Tatyana Yu. Zheleznova

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
Vladislav Yu. Shuvalov

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation
Anastasia S. Kostyuchenko

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
Alexander S. Fisyuk ∗

^aDepartment of Organic and Analytical Chemistry, Dostoevsky Omsk State University, Mira ave. 55A, Omsk 644077, Russian Federation

^bLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

Abstract

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Abstract

A one-pot method is proposed for the synthesis of 3-amino-2-arylquinolin-4(1H)-ones based on intermolecular cyclocondensation of isatoic anhydride and 1-(2-oxo-2-arylethyl)pyridinium salts in a basic medium followed by decomposition of pyridinium to amine by the action of hydrazine hydrate. The solutions of all the obtained amines emit in the blue-green region of the visible spectrum with a fluorescence quantum yield of up to 0.59 when irradiated with ultraviolet or violet light.

Key words

3-aminoquinolin-4(1H)-one - pyridinium salt - one-pot synthesis - fluorescence - microwave irradiation - quinoline - zwitterion

Full Text

References

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Supplementary Material

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