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Enaminoketone derivatives as key intermediates for the synthesis of 4-quinolones

N-substituted 4-quinolones can be obtained in good yields via intramolecular amine exchage reaction from N-substituted (E)-1-(2-aminophenyl)-3-(dimethylamino)prop-2-en-1-ones or, alternatively, from (E)-1-(2-aminophenyl)-3-(dimethylamino)prop-2-en-1-one through intramolecular amine exchange/N-benzylation. Both strategies can lead to N-(2-halobenzyl)-4-quinolones, functionalized substrates which could undergo further transformations to provide interesting polyheterocycles.

Keywords: 4-quinolone, enaminoketone, amine exchange