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Novel Synthesis of 2-Chloroquinolines from 2-Vinylanilines in Nitrile Solvent

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journal contribution
posted on 28.09.2002, 00:00 by Byoung Se Lee, Jae Hak Lee, Dae Yoon Chi
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.