New Functionalized Phenoxazines and Phenothiazines.

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: BuNH 2 , 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 BuNH 2 forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.