Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3 H -phenoxazin-3-one with ortho- substituted anilines

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3 H -phenoxazin-3-one with ortho- substituted anilines

A convenient method for the synthesis of a series of 2-(arylamino)-3 -phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3 -phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 220-250 °C is described, and the compounds...

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Veröffentlicht in:Beilstein journal of organic chemistry 2024-02, Vol.20, p.336-345
Hauptverfasser: Ivakhnenko, Eugeny, Malay, Vasily, Knyazev, Pavel, Merezhko, Nikita, Makarova, Nadezhda, Demidov, Oleg, Borodkin, Gennady, Starikov, Andrey, Minkin, Vladimir
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container_title Beilstein journal of organic chemistry
container_volume 20
creator Ivakhnenko, Eugeny
Malay, Vasily
Knyazev, Pavel
Merezhko, Nikita
Makarova, Nadezhda
Demidov, Oleg
Borodkin, Gennady
Starikov, Andrey
Minkin, Vladimir
description A convenient method for the synthesis of a series of 2-(arylamino)-3 -phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3 -phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 220-250 °C is described, and the compounds were characterized by means of single-crystal X-ray crystallography, NMR, UV-vis, and IR spectroscopy, as well as cyclic voltammetry. The reaction with -amino-, -hydroxy-, and -mercapto-substituted arylamines widened the scope and provided an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems.
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title Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3 H -phenoxazin-3-one with ortho- substituted anilines
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