New Functionalized Phenoxazines and Phenothiazines

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.

Chiral Thianthrenes

“…Our previous heterocyclic synthesis studies with 1,2-dinitro-4,5-difluorobenzene led to X-ray single-crystal determinations of phenazines, ref. [41] phenoxazines and phenothiazines [42,43]. Heterocyclic syntheses with this building block have been expanded here to explore the X-Ray single-crystal structures and stabilities of chiral, enantiomerically pure, thianthrene sulfoxides.…”