Efficient and highly selective method for the synthesis of benzo(naphtho)quinoline derivatives catalyzed by iodine.

A mild, efficient, and highly selective method for the synthesis of pyranoquinoline and furoquinoline derivatives via a three-component reaction of aromatic aldehyde, naphthalen-2-amine or anthracen-2-amine and 2,3-dihydrofuran, or 3,4-dihydro-2H-pyran catalyzed by iodine is described. It should be noted that exo-isomer was obtained with high selectivity in good yields, which was confirmed by X-ray diffraction analysis. The 3-arylbenzo(naphtha)[f]quinolines were isolated in high yields when the chain n-butylvinyl ether was used as reactant, with the unexpected loss of the butoxy group.