A new protocol for direct amination of N-Methyl-2-phenylindole catalyzed by copper(II) trifluoromethanesulfonate was presented. Both of (E)-N-(1,1'-Dimethyl-2,2'
-diphenyl-2,3'-biindolin-3-ylidene)-4-methylbenzenesulfonamide¡]4¡^and 4-methyl
-N-(1-methyl-2-phenyl-1H-indol-3-yl)benzenesulfonamide¡]2¡^were obtained under the optimal reaction conditions (2.5 mol% Cu(OTf)2, 1.2 equiv PhI=O, 0.7 equiv PhI=NTs heated at 25 ¢J in acetonitrile for 1 hour) in 78 % and 11 % yields, respectively. In addition, (E)-N-(2-hydroxy-1-methyl-2-phenylindolin-3-ylidene)-4-methylbenzene
sulfonamide ¡]6¡^and (E)-N-(1,1'-dimethyl-2,2'-diphenyl-2,3'-biindolin-3-ylidene)
-4-methylbenzenesulfonamide ¡]4¡^were synthesized in 47 % and 24 % yields, respectively, by using 5 mol% Cu(OTf)2, 2 equiv PhI=O, 1.2 equiv PhI=NTs at ambient temperature in acetonitrile for 1 hour. Finally, 4-methyl-N-(1-methyl-2-oxo-3-phenyl
indolin-3-yl)benzenesulfonamide ¡]3¡^and 1,1'-dimethyl-2,2'-diphenyl-2,3'-biindolin
-3-one ¡]7¡^can be formed under the following reaction condition, 5 mol% Cu(OTf)2, 2 equiv PhI=O, 1.2 equiv PhI=NTs and 3 equiv Ag2CO3 heated at 100 ¢J in acetonitrile for 1 hour, in 41% and 22% yields, respectively.
| Identifer | oai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0907112-135201 |
| Date | 07 September 2012 |
| Creators | Pan, Ming-kai |
| Contributors | Chiang, Michael Yen-Nan, Ming-Jung Wu, Jen-Chieh Hsieh |
| Publisher | NSYSU |
| Source Sets | NSYSU Electronic Thesis and Dissertation Archive |
| Language | Cholon |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0907112-135201 |
| Rights | user_define, Copyright information available at source archive |
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