SYNTHESIS OF 1,5-DIAZAANTHRAQUINONES AND 1,8-DIAZAANTHRAQUINONES BY REACTION OF AMINOQUINOLINEQUINONES WITH BETA-DIELECTROPHILES

Citation
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
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
51
Issue
6
Year of publication
1995
Pages
1763 - 1774
Database
ISI
SICI code
0040-4020(1995)51:6<1763:SO1A1B>2.0.ZU;2-1
Abstract
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.