10.1007/s10593-007-0106-x
The research article from "Chemistry of Heterocyclic Compounds" discusses an unexpected outcome from the interaction of 1,8-diaminonaphthalene with aromatic nitriles in polyphosphoric acid (PPA). The researchers initially expected the formation of 2-Ar-perimidines or their acylated products but instead discovered the formation of previously unknown 2,6,8-triaryl-1,3,7-triazapyrenes. The reaction mechanism is proposed to involve the formation of a 2-Ar-perimidine, followed by electrophilic attack by the nitrile cation, cyclization, and aromatization via ammonia elimination. The general method involved mixing 1,8-diaminonaphthalene, an aromatic nitrile, and PPA, stirring at 180°C, then cooling, adding water, basifying with ammonia, and extracting with ethyl acetate. The products were characterized using 1H NMR spectroscopy, and their yields and melting points were reported. The study also included elemental analysis to confirm the composition of the synthesized compounds.