Skeleton-Reorganizing Coupling Reactions of Cycloheptatriene and Cycloalkenones with Amines
© 2022 Wiley-VCH GmbH..
Skeletal reorganization reactions have emerged as an intriguing tool for converting readily available compounds into complicated molecules inaccessible by traditional methods. Herein, we report a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. In the presence of Rh/acid catalysis, cycloheptatriene can selectively couple with anilines to deliver fused 1,2-dihydroquinoline products. Mechanistic studies indicate that the retro-Mannich type ring-opening and subsequent intramolecular Povarov reaction account for the ring reorganization. Our mechanistic studies also revealed that skeleton-reorganizing amination between anilines and cycloalkenones can be achieved with acid. The synthetic utilization of this skeleton-reorganizing coupling reaction was showcased with a gram-scale reaction, synthetic derivatizations, and the late-stage modification of commercial drugs.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 62(2023), 2 vom: 09. Jan., Seite e202213074 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Ji, Ding-Wei [VerfasserIn] |
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| Links: |
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| Themen: |
1,2-Dihydroquinolines |
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| Anmerkungen: |
Date Completed 04.01.2023 Date Revised 09.02.2023 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/anie.202213074 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM348862970 |
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| 520 | |a © 2022 Wiley-VCH GmbH. | ||
| 520 | |a Skeletal reorganization reactions have emerged as an intriguing tool for converting readily available compounds into complicated molecules inaccessible by traditional methods. Herein, we report a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. In the presence of Rh/acid catalysis, cycloheptatriene can selectively couple with anilines to deliver fused 1,2-dihydroquinoline products. Mechanistic studies indicate that the retro-Mannich type ring-opening and subsequent intramolecular Povarov reaction account for the ring reorganization. Our mechanistic studies also revealed that skeleton-reorganizing amination between anilines and cycloalkenones can be achieved with acid. The synthetic utilization of this skeleton-reorganizing coupling reaction was showcased with a gram-scale reaction, synthetic derivatizations, and the late-stage modification of commercial drugs | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
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| 650 | 4 | |a Cycloalkenones | |
| 650 | 4 | |a Cycloheptatrienes | |
| 650 | 4 | |a Hydroamination | |
| 650 | 4 | |a Skeleton Reorganization | |
| 650 | 7 | |a Amines |2 NLM | |
| 650 | 7 | |a Aniline Compounds |2 NLM | |
| 700 | 1 | |a Hu, Yan-Cheng |e verfasserin |4 aut | |
| 700 | 1 | |a Min, Xiang-Ting |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Heng |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Wei-Song |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Yongjin J |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Qing-An |e verfasserin |4 aut | |
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