Abstract
Reactions of N-oxides of lepidine (1a) and 4-methyl- (1b), 4-chloro- (1c) and 6-methoxyquinoline (1d) with tosyl chloride (1 eq) and triethylamine (ca. 10 eq) in a mixture of chloroform and water at room temperature gave the corresponding di (2-quinolyl) ethers (3a-d) and N-(2-quinolyl)-2-quinolones (4a-d). The efficiency of this type of reaction depends upon the nature and position of the substituents. Whereas the reaction of 1c with carbostyril under the same conditions gave small amounts of 4-chloro-2-tosyloxyquinoline (2c) and N-(4-chloro-2-quinolyl)-4-chloro-2-quinolone (4c), that of 1d afforded 6-methoxy-2-quinolyl 2'-quinolyl ether (15) and N-(6-methoxy-2-quinolyl)-2-quinolone (16) in 47 and 29% yields, respectively.
