N-Oxides of azaanthraquinones

The redox propexties of a series of l-azaanthracene-9,10-diones, l$-diazaanthracene-9,10-diones, 1 $-diazaanthracene-(lH)2,9,1O-triones and 1,8-diazaanthracene-(lH, 8H)2,7,9,lO-terraones have been studied. The results obtained show that the 2-pyridone moiety is a stronger electron acceptor than the pyridine ring, in agreement with reactivity data. 1-Hydroxy-lazaanthracene-2,9,10-triones, synthesized from l-azaanthracene-9,1O-dione-N-oxides, show redox properties close to 1,8-diazaanthracene-2,7,9,lO-tetraones, and therefore the cyclic hydroxamic acid unit behaves also as an strong electron acceptor. Voltammetric half-wave fist potentials correlate with the energies of the LUMO in model compounds. INTRODUCTIONThe redox properties of heterocyclic quinones have attracted considerable interest1 and their study is of relevance in the understanding of the biological roles of these compounds. Many well-known antitumour agents, including mitoxantrone, the anthracyclines, the naphthyridinomycinsaframycin family, and the mitomycins have a quinone

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Half‐Wave Potentials of 1‐AZA‐ and 1,8‐Diazaanthraquinones

Diaz‐Guerra

Ocaña

Pérez

et al. 1995

Bulletin des Soc Chimique

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ChemInform Abstract: N‐Oxides of Azaanthraquinones.

1994

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General preparative route to benzo[g]quinolines (1‐azaanthracenes)

Krapcho¹,

Gilmor²

1999

Journal of Heterocyclic Chem

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A convenient synthetic pathway to benzo[g]quinolines (1‐azaanthracenes) has been developed. The nickel catalyzed coupling of methyl 2‐chloronicotinate (3a) with benzylic organo zinc reagents 2a‐e led to the methyl 2‐benzylic substituted nicotinates 4a‐e. Treatment of methyl 2‐chloro‐6‐methylnicotinate (3b)with 2a in a similar manner led to methyl 2‐benzyl‐6‐methyInicotinate (4f). The coupling of 2‐chloro‐3‐acetylpyridine (5) with benzyl zinc bromide (2a) led to 2‐benzyl‐3‐acetylpyridine (4g). The coupling of the 2,5‐dichlorobenzylic organic zinc reagent (2f) with methyl 2‐choronicotinate (3a) was unselective but readily coupled with methyl 2‐bromonicotinate (6) to yield methyl 2‐(2,5‐dichlorobenzyl)nicotinate (4h). The esters 4a‐f,h on reduction with lithium aluminum hydride led to the corresponding alcohols 7a‐f,h which were subsequently oxidized with manganese dioxide to the respective 2‐benzylic substituted pyridine‐3‐carboxaldehydes 8a‐f,h. In one case the coupling of benzy] zinc bromide (2a) with 2‐chloropyridine‐3‐carboxaldehyde (9) led directly to 2‐benzylpyridine‐3‐carboxaldehyde (8a), but in poor yield. Cyclizations of the aldehydes 8a‐d,f,h or the ketone 4g with polyphosphoric acid afforded the benzo[g]quinolines 10a‐d,f‐h in high yields. Aldehyde 8e was cyclized to 10e using a solution of sulfuric acid in methanol. Several of the benzo[g]quinolines 10c,d could be readly converted into the benzo[q]quinoline‐5,10‐diones 11c,d on treatment with ammonium ceric nitrate.

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N-Oxides of azaanthraquinones

Cited by 12 publications

References 24 publications

Half‐Wave Potentials of 1‐AZA‐ and 1,8‐Diazaanthraquinones

Half‐Wave Potentials of 1‐AZA‐ and 1,8‐Diazaanthraquinones

ChemInform Abstract: N‐Oxides of Azaanthraquinones.

General preparative route to benzo[g]quinolines (1‐azaanthracenes)

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