キノリン核合成に関する研究 (第3報)
1961 年 81 巻 6 号 p. 855-860
詳細
1961 年 81 巻 6 号 p. 855-860
The quinoline containing radioactive carbon, obtained by the reaction of aniline and acrolein [3-14C] diacetate, was derived through its 1-oxide to carbostyryl, oxidized with potassium permanganate to kynuric acid, and hydrolyzed into oxalic acid and anthranilic acid. The radioactive carbon was found to be in oxalic acid. This has revealed that the synthesis of quinoline from aniline and acrolein was effected by the mechanism (a) in Chart 1.
The reaction of quinoline synthesis from aromatic primary amines and acrolein diacetate is affected by the acidity of the reaction mixture and the yield varies through the maximum with increasing acidity, In the case of p-nitroaniline, with weaker basicity than aniline, the optimal acidity is higher than that of aniline and this phenomenon can be explained by detailed analysis of the mechanism (a) shown in Chart 1.
