Abstract
Application of tosyl chloride to 4-chloroquinoline 1-oxide in the presence of pyridine gives 1-(4-chloro-2-quinolyl) pyridinium chloride (II). The same reaction with 2-quinolinol 1-oxide (III) produces 89.5% of 8-toxyloxycarbostyril (IV) and 8.5% of 1-(2-hydroxy-6-quinolyl) pyridinium chloride (V) when 1 equivalent of tosyl chloride is used, and 81.9% of 2, 8-ditosyloxyquinoline (IV′) and 15.5% of V when 2 equivalents of tosyl chloride is used. The same reaction of 4-quinolinol 1-oxide (VIII) produces 46-61% of 3-tosyloxy-4-quinolone (IX) and 31-45% of 1-(4-hydroxy-6-quinolyl) pyridinium salt (X), 1-Isoquinolinol 2-oxide produced only 4-tosyloxyisocarbostyril (XIII) by the same reaction. Considerations were made on the reaction mechanism of III, VIII, and XII and general characteristics of this reaction was clarified.
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