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

The isocoumarin derivative 1H-1w-acetylimino-3-methylbenzo[c]pyran-4-carbon itrile reacts with 1,8-naphthalenediamine under basic conditions to give, p rimarily, 12-acetylisoquino[2,1-a]perimidin-13-amine This undergoes a varie ty of reactions to give other isoquino[2,1-a]perimidine derivatives, ring o pening to 2-(1H-perimidin-2-yl)phenylacetic acid derivatives and, in polyph osphoric acid, a new hexacyclic system, 6-methyl-7,13,13d-triazadibenzo[def ;qr]chrysene.