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

Eugeny P. Ivakhnenko; Vasily I. Malay; Pavel A. Knyazev; Nikita I. Merezhko; Nadezhda I. Makarova; Oleg P. Demidov; Gennady S. Borodkin; Andrey G. Starikov; Vladimir I. Minkin

doi:10.3762/bxiv.2023.53.v1

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

Eugeny P. Ivakhnenko ,
Vasily I. Malay ,
Pavel A. Knyazev ,
Nikita I. Merezhko ,
Nadezhda I. Makarova ,
Oleg P. Demidov ,
Gennady S. Borodkin ,
Andrey G. Starikov and
Vladimir I. Minkin

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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Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.20.34

SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)