Journal of Organic Chemistry 2002-11-01

Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent.

Byoung Se Lee, Jae Hak Lee, Dae Yoon Chi

Index: J. Org. Chem. 67(22) , 7884-6, (2002)

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Abstract

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.