Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent.
2-Vinyl- or heteroaryl-substituted anilines were reacted with diphosgene in acetonitrile solution via a reactive imidoyl moiety to afford the corresponding 2-chloroquinolines. Facile syntheses of nine 2-chloroquinoline derivatives from several anilines and their postulate mechanism is described. The postulate mechanism of 2-chloroquinoline formation via imidoyl moiety as a good leaving group shows that the reaction consists of the following three steps: (1) generation of phenylisocyanate, (2) quinoline ring formation, and (3) chlorination on C2 position of quinoline.
Lee
Byoung Se
BS
Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea.
Lee
Jae Hak
JH
Chi
Dae Yoon
DY