Facile Approach to the N,O,S-Heteropentacycles via Condensation of Sterically Crowded 3H-Phenoxazin-3-one with ortho-amino-, hydroxy- and mercaptoanilines

Submitting author affiliation:
Southern Federal University, Rostov-on-Don, Russian Federation

Beilstein Arch. 2023, 202353. https://doi.org/10.3762/bxiv.2023.53.v1

Published 27 Nov 2023

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A convenient method for the synthesis of a series of 2-arylamino-3H-phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3H-phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 230-250 °C is described and the compounds are characterized by means of single-crystal X-ray crystallography, NMR, UV/vis, IR spectroscopy and cyclic voltammetry. Involvement into the reaction of arylamines with o-amino-, o-hydroxy and o-mercapto-substituents widens its scope and provides for an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems.

Keywords: 3H-phenoxazin-3-one; pentacyclic heterocycles; synthesis; fluorescence; molecular structure

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Ivakhnenko, E. P.; Malay, V. I.; Knyazev, P. A.; Merezhko, N. I.; Makarova, N. I.; Demidov, O. P.; Borodkin, G. S.; Starikov, A. G.; Minkin, V. I. Beilstein Arch. 2023, 202353. doi:10.3762/bxiv.2023.53.v1

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