含窒素複素環化合物の研究(第36報)含窒素複素環化合物に対するvon Braun反応の改良とQuinaldineからの3-Bromoquinaldineの合成法

概要

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Treatment of commercially easily available quinoline, isoquinoline, benzo [f] quinoline, 5-, 6-, or 8-nitroquinoline, 2-, 4-, 6-, 7-, or 8-methylquinoline, and 6-methoxyquinoline with cyanogen bromide and sodium hydrogen carbonate in methanol affords the corresponding 1-cyano-2-methoxy-1,2-dihydroquinolines and 2-cyano-1-methoxy-1,2-dihydro-isoquinolines in a high yield. The yield of the objective compounds from this reaction is about twice that of the von Braun reaction not using sodium hydrogen carbonate. By the use of this reaction, synthesis of 3-bromoquinaldine, which had been difficult to synthesize heretofore, was established, and synthetic method for 3-bromo-4-(or 6-, 7-, 8-)-methylquinolines was also improved.
公益社団法人日本薬学会の論文
1979-05-25