A. Marcos et al., SYNTHESIS OF 1,5-DIAZAANTHRAQUINONES AND 1,8-DIAZAANTHRAQUINONES BY REACTION OF AMINOQUINOLINEQUINONES WITH BETA-DIELECTROPHILES, Tetrahedron, 51(6), 1995, pp. 1763-1774
Easily obtained amino derivatives of quinoline-5,8-quinone (1 and 2) a
nd 4-methyl(1H)2,5,8-quinolinethrione (3) react with beta-dielectrophi
les, affording aminoalkylidenemalonates in a convenient procedure. The
se compounds cyclise thermally to 1,5-diaza-(1H)4,9,10-anthracenetrion
es (10 and 19), 1,8-diaza-(1H)4,9,10-anthracenetriones (11 and 20) and
15-diaza-(1H, 5H)2,8,9,10- anthracenetetraones (12 and 21). The strat
egy is less convenient when applied to aromatic precursors, Knorr cycl
isation of beta-oxoanilides fails in both systems.