Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent |
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Authors: | Lee Byoung Se Lee Jae Hak Chi Dae Yoon |
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Institution: | Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea. |
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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. |
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