Synthesis of some 2-alkyl-4-quinolone and 2-alkyl-4-methoxyquinoline alkaloids

Acid-catalyzed condensation of a series of 3-oxoalkanoic acid esters with aniline affords the corresponding 2-alkyl-4-quinolones in good yield. Treatment of these compounds with methyl iodide affords 2-alkyl-4-methoxyquinolines and 2-alkyl-N-methylquinolones. Three of the compounds are naturally-occurring alkaloids which are synthesized here for the first time.