Synthesis of 1,5- and 1,8-diazaanthraquinones by reaction of aminoquinolinequinones with β-dielectrophiles

Article abstract of DOI:10.1016/0040-4020(94)01048-5

Easily obtained amino derivatives of quinoline-5,8-quinone (1 and 2) and 4-methyl-(1H)2,5,8-quinolinetrione (3) react with β-dielectrophiles, affording aminoalkylidenemalonates in a convenient procedure. These compounds cyclise thermally to 1,5-diaza-(1H)4,9,10-anthracenetriones (10 and 19), 1,8-diaza-(1H)4,9,10-anthracenetriones (11 and 20) and 1,5-diaza-(1H, 5H)2,8,9,10-anthracenetetraones (12 and 21). The strategy is less convenient when applied to aromatic precursors. Knorr cyclisation of β-oxoanilides fails in both systems.