Synthesis of pyrimido[5,4-c]quinolines and related quinolines as potential antimalarials

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Abstract
3-Ethylaminomethyl-2-methyl-4(1H)-quinolone and its 6-CH3, 6-OCH3 and 7-Cl derivatives were prepared by means of the Mannich reaction. Conversion to the 4-chloro derivatives and condensation with 3-chloroaniline gave the corresponding 4-(3-chloroanilino) derivatives. Cyclization of 4-(3-chloroanilino)-2,6-dimethyl-3-ethylaminomethylquinoline and its 6-OCH3 derivative with paraformaldehyde gave 1-(3-chlorophenyl)-3,9-dimethyl-3-ethyltetrahydropyrimido[5,4-c]quinoline and the 9-OCH3 derivative 4b. Treatment of 4b with benzaldehyde gave 1-(3-chlorophenyl)-3-ethyl-9-methoxy-5-styryltetrahydropyrimido[5,4-c]quinoline. 3-Benzylaminomethyl-6-methoxy-2-methyl-4(1H)-quinolone and 3,3''-(1,3-benzyliminodimethylene)di[2-methyl-4(1H)-quinolone] were also synthesized. The compounds were inactive as antimalarials.