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Nucleophilic reactions of l‐methyl‐2‐methoxy‐2‐phenyl‐3‐oxo‐2,3‐dihydroindole
Author(s) -
KeQing Ling
Publication year - 1996
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19960140313
Subject(s) - chemistry , nucleophilic substitution , nucleophile , aluminum hydride , methanol , medicinal chemistry , lithium (medication) , hydride , methylene , nucleophilic aromatic substitution , substitution reaction , organic chemistry , catalysis , hydrogen , medicine , endocrinology , methoxide
The title compound (1) was prepared via methylene blue (MB)‐sensitized photooxy‐genation of l‐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). Reduction of 1 with lithium aluminum hydride, followed by acidic workup yielded 4d and 2d, whereas the same reduction reaction of 1, followed by neutral workup gave l‐methyl‐2‐phenyl‐3‐hydroxy‐2,3‐dihydroindole (15), together with 3. The reaction pathways of nucleophilic substitution and reduction of 1 were discussed.