Synthesis, antimalarial activity, and phototoxicity of some benzo[h]quinoline-4-methanols

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Abstract
Nine .alpha.-dibutylaminomethylbenzo[h]quinoline-4-methanols were synthesized from the corresponding 1-aminonaphthalenes by the following sequence: 1-aminonaphthalene .fwdarw. 1H-benz[g]indole-2,3-dione .fwdarw. benzo[h]quinoline-4-carboxylic acid .fwdarw. acid chloride .fwdarw. bromomethyl ketone .fwdarw. epoxide .fwdarw. benzo[h]quinoline-4-methanol. Several acid chlorides substituted in the 3 position reacted incompletely with ethereal diazomethane but were efficiently converted, without isolation of the intermediates, to the bromomethyl ketones by reaction with ethoxymagnesium diethylmalonate, bromination, hydrolysis and decarboxylation. Several compounds prepared, especially .alpha.-dibutylaminomethyl-2-(2'',4''-dimethylphenyl)-3-methyl-6-chlorobenzo[h]quinoline-4-methanol; showed significant antimalarial activity against Plasmodium berghei in infected mice but were moderately phototoxic.

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