Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin

Article abstract of DOI:10.1002/jhet.5570350633

The isocoumarin derivative 1H-1-acetylimino-3-methylbenzo[c]pyran-4- carbonitrile reacts with 1,8-naphthalenediamine under basic conditions to give, primarily, 12-acetylisoquino[2,1-a]perimidin-13-amine. This undergoes a variety of reactions to give other isoquino[2,1-a]perimidine derivatives, ring opening to 2-(1H-perimidin-2-yl)phenylacetic acid derivatives and, in polyphosphoric acid, a new hexacyclic system, 6-methyl-7,13,13d- triazadibenzo[def,qr]chrysene.