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.
Wang
Xiang-Shan
XS
School of Chemistry and Chemical Engineering, Xuzhou Normal University, The Key Laboratory of Biotechnology on Medical Plant, Xuzhou Jiangsu 221116, P.R. China. xswang1974@yahoo.com
Zhou
Jie
J
Yin
Ming-Yue
MY
Yang
Ke
K
Tu
Shu-Jiang
SJ
D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D008958:Models, Molecular; D011804:Quinolines / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
D011804:Quinolines; D007455:Iodine