臺灣博碩士論文加值系統

利用2-(2-alkylethynyl) benzonitrile以甲醇鈉來處理可得到適中產率
的3-alkyl-1(2H)-isoquinolinone，在相同的反應條件下，同樣以2-(2-
arylethynyl)benzonitrile來進行甲醇水解反應則會導致3-alkylidene
isoindol-1-one的形成。若將2-(1-hexynyl) benzonitrile行部份水解可
得到對映的benzamide，然後再將此benzamide以甲醇鈉來處理可獲得11
%產率的3-pentylidene isoindol-1-one；這個結果顯示benzamide並非形
成isoquinolinone過程中的中間體。對這個甲醇水解過程的反應機制作較
合理的解釋是：先形成iminium anion(亞胺陰離子) ，再進行芳香性環化
反應形成2-methoxyisoquinoline，然後接著水解可得到isoquinolinone
，在其中的一個例子中，2-methoxyisoquinoline產物也被分離出來。

The treatment of 2-(2-alkylethynyl) benzonitrile with sodium
methoxide in methanol gave 3-alkyl-1(2H)-isoquinolinone in
modest yield. Under the same reaction conditions methanolysis of
2-(2-arylethynyl)benzonitrile lead to the formation of
3-alkylidene isoindol-1-one. Partial hydrolysis of 2-
(1-hexynyl) benzonitrile to the corresponding benzamide,
followed by the treatment of the benzamide with sodium methoxide
gave 3-pentylidene isoindol-1-one in 11% yield. This result
suggests that benzamide is not the intermediate in the formation
of isoquinolinone. The more plausible mechanism of this
methanolysis process involved the iminium anion
cycloaromatization to form 2-methoxyisoquinoline with
subsequently hydrolyzed into isoquinolinone. In one case,
2-methoxyisoquinoline product was isolated.