1962 年 82 巻 11 号 p. 1532-1537
Diphenyliodonium bromide (DIB) was reacted with various phenols either in its potassium salts or in the presence of potassium carbonate. It was found that the elevation of the reaction temperature in DME as a solvent shorten the reaction period (Table I). Even when nitro or acetyl group which may hinder sterically or form chelation at ortho position of the hydroxyl groups, the reaction was recognized to take place (Table II). The syntheses of (V) R=H and (IX) R=H were successful applying the reaction of Chart 2.
Phenylation of heterocyclic aromatic compounds, such as 8-quinolinol and carbostyril (X) (Chart 3) with DIB afforded 8-phenoxyquinolinol, 2-phenoxyquinolinol, 3-phenylcarbostyril and the substance of m.p. 169-171°, whose structure was unknown. In this reaction, 1-phenylcarbostyril had not been obtained.