As part of our program on the synthesis of new psychotropic agents, the parent rings of two diazaphenox-azines are described. The reaction of 2-aminophenol and 2,3-dichloropyrazine in alkaline media gave good yields of 1,4-diazaphenoxazine. Replacement of 2,3-dichloropyrazine with 2,3-dichloroquinoxaline gave on the other hand the heterocycle, 1,4-diazabenzo[b]phenoxazine. Nitration and S-oxide formation were achieved by reaction with mixed nitric and sulfuric acids. Mechanistic pathways to these compounds were also discussed.
Journal of Heterocyclic Chemistry 11/1981; 18(7):1445 – 1449. DOI:10.1002/jhet.5570180732