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

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