1979 年 99 巻 12 号 p. 1240-1244
Reaction of quinoline (I) and isoquinoline (VI) with diborane, followed by treatment with hydrochloric acid, afforded the corresponding 1, 2, 3, 4-tetrahydro compounds. However, quinaldine (III) gave traces of 1, 2, 3, 4-tetrahydroquinaldine, and neither lepidine (V) nor 3-methylisoquinoline (VIII) were reduced under similar conditions. On the other hand, quinoxaline derivatives reacted with diborane alone to give the corresponding 1, 2, 3, 4-tetrahydro derivatives in quantitative yields. It is interesting that the reduction of heteroaromatic compounds proceeded with diborane.