Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1-Methyl-8-dimethylamino-10-phenylphenazin-2-(10H)one and Related Compounds

M John Plater; William T A Harrison

doi:10.1002/open.202300007

Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1-Methyl-8-dimethylamino-10-phenylphenazin-2-(10H)one and Related Compounds

M John Plater^* (Corresponding Author), William T A Harrison

^*Corresponding author for this work

Chemistry

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Abstract

Oxidative condensation of three p-phenylenediamines with 3-hydroxy-2-methyl-N-(phenylamino)benzene gives new coloured aposafranones. 2-Methylresorcinol is easy to convert into the asymmetric building block 3-hydroxy-2-methyl-N-(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1-methyl and N-phenyl groups. The UV/Vis absorption maxima are in the range 530-545 nm.

Original language	English
Article number	e202300007
Number of pages	6
Journal	ChemistryOpen
Volume	12
Issue number	2
Early online date	13 Feb 2023
DOIs	https://doi.org/10.1002/open.202300007
Publication status	Published - 13 Feb 2023

Bibliographical note

Acknowledgements
We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-raydata collections.

Data Availability Statement

ticle.
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this

Keywords

aposafranone
Chromophores
phenazinone
safranone
X-ray crystallography

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Cite this

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title = "Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1-Methyl-8-dimethylamino-10-phenylphenazin-2-(10H)one and Related Compounds",

abstract = "Oxidative condensation of three p-phenylenediamines with 3-hydroxy-2-methyl-N-(phenylamino)benzene gives new coloured aposafranones. 2-Methylresorcinol is easy to convert into the asymmetric building block 3-hydroxy-2-methyl-N-(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1-methyl and N-phenyl groups. The UV/Vis absorption maxima are in the range 530-545 nm.",

keywords = "aposafranone, Chromophores, phenazinone, safranone, X-ray crystallography",

author = "Plater, {M John} and Harrison, {William T A}",

note = "Acknowledgements We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-raydata collections. ",

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T2 - Structure of 1-Methyl-8-dimethylamino-10-phenylphenazin-2-(10H)one and Related Compounds

AU - Plater, M John

AU - Harrison, William T A

N1 - Acknowledgements We thank the UK EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the UK National Crystallography Centre (University of Southampton) for the X-raydata collections.

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Y1 - 2023/2/13

N2 - Oxidative condensation of three p-phenylenediamines with 3-hydroxy-2-methyl-N-(phenylamino)benzene gives new coloured aposafranones. 2-Methylresorcinol is easy to convert into the asymmetric building block 3-hydroxy-2-methyl-N-(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1-methyl and N-phenyl groups. The UV/Vis absorption maxima are in the range 530-545 nm.

AB - Oxidative condensation of three p-phenylenediamines with 3-hydroxy-2-methyl-N-(phenylamino)benzene gives new coloured aposafranones. 2-Methylresorcinol is easy to convert into the asymmetric building block 3-hydroxy-2-methyl-N-(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1-methyl and N-phenyl groups. The UV/Vis absorption maxima are in the range 530-545 nm.

KW - aposafranone

KW - Chromophores

KW - phenazinone

KW - safranone

KW - X-ray crystallography

U2 - 10.1002/open.202300007

DO - 10.1002/open.202300007

M3 - Article

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SN - 2191-1363

VL - 12

JO - ChemistryOpen

JF - ChemistryOpen

IS - 2

M1 - e202300007

ER -

Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1-Methyl-8-dimethylamino-10-phenylphenazin-2-(10H)one and Related Compounds

Abstract

Bibliographical note

Data Availability Statement

Keywords

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