New Functionalized Phenoxazines and Phenothiazines

M John Plater; William T A Harrison

doi:10.1021/acsomega.3c06461

New Functionalized Phenoxazines and Phenothiazines

ACS Omega. 2023 Nov 9;8(46):44163-44171. doi: 10.1021/acsomega.3c06461. eCollection 2023 Nov 21.

Authors

M John Plater¹, William T A Harrison¹

Affiliation

¹ Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, United Kingdom of Great Britain and Northern Ireland.

Abstract

The reaction of either 2-aminophenol or 2-(N-methylamino)phenol with 1,2-difluoro-4,5-dinitrobenzene and sodium carbonate in EtOH gives 2,3-dinitrophenoxazines. One nitro group, conjugated to the aryl ether, was displaced from 2,3-dinitro-10-methylphenoxazine with different nucleophiles: BuNH₂, KOEt, and KOH. The reaction of 2-aminothiophenol with 1,2-difluoro-4,5-dinitrobenzene under the same conditions gives 2,3-dinitrophenothiazine. This reacted with BuNH₂ forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.