The synthesis of three new azaphenothiazine ring systems and an evaluation of their use as intermediates for new dyes and pigments is described. 2-Amino-5-bromopyrazine-3[4H]-thione (11) was prepared and converted to the novel 1,4,6,9-tetraazaphenothiazine ring system. The reaction of 4,5-diaminopyrimidine-6[1H]-thione (15) with 2,3-dichloropyrazines gave the isomeric 1,4,6,8-tetraazaphenothiazine ring system, another new heterocycle in this series. With 2,3-dichloroquinoxaline a previously unknown tetracyclic tetraazaphenothiazine ring system was isolated in satisfactory yields. The properties and reactions of these new heterocyclic systems are presented. Mixed nitric and sulphuric acids convert them to their 5-sulphoxides. Structural assignments were based on chemical evidence and their UV, IR, NMR and mass spectra. Mechanistic pathways to these compounds are also proposed.
Dyes and Pigments 12/1985; 6(6):405-415. DOI:10.1016/0143-7208(85)80022-X