Synthesis of Acylaminoperimidines by the Reaction of 1,8-Naphthylenediamine with Nitroketones

The reaction of 1,8-naphthylenediamine with α-nitoketones yielded 9-acetyl- and 6(7)-acetamidoperimidines. The reaction exhibits high atom economy and is based on a tandem of benzoylation reactions of the diamine involving nitoketones, and an acylation-amination of arenes in polyphosphoric acid (PPA) medium, using the acyl forms of nitroalkanes liberated in the first stage. The dependence of the transformation’s course on the concentration of polyphosphoric acid has been investigated.