The title compound (1) was prepared via methylene blue (MB)-sensitized photooxygenation of 1-methyl-2-phenylindole (2d) in methanol. Acid-catalyzed nucleophilic substitution of 1 with nucleophiles gave 1,2,2-trisubsti...The title compound (1) was prepared via methylene blue (MB)-sensitized photooxygenation of 1-methyl-2-phenylindole (2d) in methanol. Acid-catalyzed nucleophilic substitution of 1 with nucleophiles gave 1,2,2-trisubstituted 3-oxo-2,3-dihydroindoles (3-6). lithium aluminum hydride, followed by acidic workup yielded 4d and 2d, whereas the same reduction reaction of 1, followed by neutral workup gave 1-methyl-2-phenyl-3-hydroxy-2,3-dihydroindole (15), together with 3. The reaction pathways of nucleophilic substitution and reduction of 1 were discussed.展开更多
基金Project supported by the Coal Industry Universities Science Foundation of China.
文摘The title compound (1) was prepared via methylene blue (MB)-sensitized photooxygenation of 1-methyl-2-phenylindole (2d) in methanol. Acid-catalyzed nucleophilic substitution of 1 with nucleophiles gave 1,2,2-trisubstituted 3-oxo-2,3-dihydroindoles (3-6). lithium aluminum hydride, followed by acidic workup yielded 4d and 2d, whereas the same reduction reaction of 1, followed by neutral workup gave 1-methyl-2-phenyl-3-hydroxy-2,3-dihydroindole (15), together with 3. The reaction pathways of nucleophilic substitution and reduction of 1 were discussed.
