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

Research output: Contribution to journal › Article › peer-review

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

Keywords

aposafranone
Chromophores
phenazinone
safranone
X-ray crystallography

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10.1002/open.202300007Licence: CC BY-NC

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© 2023 The Authors. Published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial. https://creativecommons.org/licenses/by-nc/4.0/
Final published version, 1.12 MBLicence: CC BY-NC

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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. ",

year = "2023",

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day = "13",

doi = "10.1002/open.202300007",

language = "English",

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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.

PY - 2023/2/13

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

C2 - 36782392

VL - 12

JO - ChemistryOpen

JF - ChemistryOpen

SN - 2191-1363

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

Keywords

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