Acridine-1,8-dione derivatives

Several classes of ligands have been described such as porphyrins, perylenes, amidoanthracene-9,10-diones, 2,7-disubstituted amidofluoren-ones, acridines, ethidium derivatives,disubstituted triazines, fluoroquinoanthroxazines, indoloquinolines, dibenzophenanthrolines, ... 

Tu SJ, Jiang B, Jia RH (2006) An efficient one-pot, three-component synthesis of indeno [1, 2-b]quinoline-9, 11(6H, 10H)-dione, acridine-1, 8(2H, 5H)-dione and quinoline-3-carbo-nitrile derivatives from enaminones. Org Biomol Chem 4 3664—3668... 

Alkylation of isoquinolinone by Michael reaction followed by acid-catalyzed cyclization is used to prepare acridine-1,9-diones <97SC95>. The oxidation of these compounds to the 1-hydroxyacridones has been applied to acridine alkaloids <97T12717>. The reaction of the 2-amino-1,3-diene with the quinolinone 52 affords the acridine derivative 53 directly <97JCS(P1)2807>. 

A set of new two-carbon-tethered fused acridine/indoles 62 were synthesized via a AcOH-promoted domino reaction of indoline-2,3-dione 61 and C2-tethered indol-3-yl enaminones 57a (Scheme 12.22) [43]. The reaction was further expanded to prepare C-tethered fused acridine/pyridines pairs, N-substituted amino acids, N-cyclopropyl, and N-aryl-substituted fused acridine derivatives. In these domino processes, a fused acridine skeleton with concomitant formation of two new rings was readily achieved in good yields. 

Reaction with 2-Aminoquinones. Acyl and carbox3miethyl radicals generated using Mn(OAc)3 react with 2-aminoquinones in a fashion similar to that of their naphthoquinone counterparts. In case of 2-arylainino-l,4-benzoquinones, sequential radical addition/cycUzation occurs to afford the corresponding acridine derivatives (eq 34). The yield is lowered in the presence of an electron-withdrawing group on the aniline. Benzo[/]-indole-4,9-diones and their derivatives can be obtained exclusively with... 

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