Selective Synthesis of 3-(9 H-Carbazol-2-yl)indolin-2-ones and Spiro[tetrahydrocarbazole-3,3'-oxindoles] via a HOTf Catalyzed Three-Component Reaction
Yang, RY; Sun, J; Sun, Q; Yan, CG
| HERO ID | 5415119 |
|---|---|
| In Press | No |
| Year | 2018 |
| Title | Selective Synthesis of 3-(9 H-Carbazol-2-yl)indolin-2-ones and Spiro[tetrahydrocarbazole-3,3'-oxindoles] via a HOTf Catalyzed Three-Component Reaction |
| Authors | Yang, RY; Sun, J; Sun, Q; Yan, CG |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue | 11 |
| Page Numbers | 5909-5919 |
| Abstract | A HOTf catalyzed three-component reaction of indoles, acetophenones, and ( E)-3-phenacylideneoxindolinones resulted in the unexpected polysubstituted 3-(9 H-carbazol-2-yl)indolin-2-ones in good yields. A similar reaction with various cyclic ketones afforded the corresponding carbocyclic fused 3-(9 H-carbazol-2-yl)indolin-2-ones. On the other hand, ( E)-3-arylideneoxindolinones in the three-component reaction gave the expected spiro[tetrahydrocarbazole-3,3'-oxindoles] through a domino alkenylation/Diels-Alder reaction. The unusual different reactivity of ( E)-3-phenacylideneoxindolinones and ( E)-3-arylideneoxindolinones in the three-component reactions was believed to involve the different reaction paths caused by the existence of the carbonyl group. |
| Doi | 10.1021/acs.joc.8b00196 |
| Pmid | 29696973 |
| Wosid | WOS:000434367700003 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |