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

Autor: Eugeny Ivakhnenko, Vasily Malay, Pavel Knyazev, Nikita Merezhko, Nadezhda Makarova, Oleg Demidov, Gennady Borodkin, Andrey Starikov, Vladimir Minkin
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 336-345 (2024)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.20.34
Popis: 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 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 o-amino-, o-hydroxy-, and o-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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