Synthesis of 8-amino- and 8-acetyl(benzoyl) aminomackinazolinones and their condensation with aldehydes

Methods for preparing of 8-nitro- and 8-aminomackinazolinones were improved. 8-Acetyl(benzoyl)aminomackinazolinones reacted smoothly with aromatic aldehydes and furfurol in glacial acetic acid to give the corresponding 4-arylidene-substituted derivatives. Reaction of 8-aminomackinazolinone with aromatic aldehydes in glacial acetic acid was accompanied by acetylation of the amine and gave 8-acetylamino-4-arylidenemackinazolinones. Reaction of 8-aminomackinazolinone and p-nitrobenzaldehyde in propionic acid produced 8-[(4' -nitrobenzylidene)amino]-4-(4aEuro(3)-nitrobenzylidene)mackinazolinone. In contrast, the reaction in Py occurred selectively at the amine to form the corresponding Schiff base 8-[(4'-nitrobenzylidene)amino]mackinazolinone.