| Nucleophilic reactions of 1-methyl-2-methoxy-2-phenyl-3-oxo-2,3-dihydroindole |
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| 作者姓名： | LING Ke-Qing |
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| 作者单位： | LING，Ke-QingDepartment of Chemistry，Huaibei Coal Industry Teacher's College，Huaibei，Anhui 235000，China |
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| 基金项目： | Project supported by the Coal Industry Universities Science Foundation of China. |
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| 摘 要： | 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.
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Nucleophilic reactions of 1-methyl-2-methoxy-2-phenyl-3-oxo-2,3-dihydroindole |
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| LING,Ke-Qing.Nucleophilic reactions of 1-methyl-2-methoxy-2-phenyl-3-oxo-2,3-dihydroindole[J].Chinese Journal of Chemistry,1996(3). |
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| Authors: | LING Ke-Qing |
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| Institution: | LING,Ke-QingDepartment of Chemistry,Huaibei Coal Industry Teacher's College,Huaibei,Anhui 235000,China |
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| Abstract: | 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. |
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| Keywords: | 1-Methyl-2-methoxy-2-phenyl-3-oxo-2 3-dihydroindole nucleophilic substitution duction |
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