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

ChemistryOpen. 2023 Feb;12(2):e202300007. doi: 10.1002/open.202300007.

Authors

M John Plater¹, William T A Harrison¹

Affiliation

¹ Department of Chemistry, University of Aberdeen Meston Walk, Aberdeen, AB24 3UE, United Kingdom.

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: X-ray crystallography; aposafranone; chromophores; phenazinone; safranone.

Grants and funding

UK EPSRC National Mass Spectrometry Service Centre