Tetrahedron p. 1763 - 1774 (1995)
Update date:2022-07-30
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Marcos, Alicia
Pedregal, Carmen
Avendano, Carmen
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.
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