Skeletal Editing of Benzene Motif : Photopromoted Transannulation for Synthesis of DNA-Encoded Seven-Membered Rings
In this report, we present a photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif coupled with a Reversible Adsorption to Solid Support (RASS) strategy. A variety of valuable DNA-encoded seven-membered ring compounds, including DNA-encoded 3H-azepines, azepinones, and unnatural amino acids, are now accessible. Crucially, this DNA-compatible protocol can also be applied for the introduction of complex molecules, as exemplified by Lorcaserin and Betahistine. The selective conversion of readily available phenyl rings into high-value seven-membered rings offers a promising avenue for the construction of diversified and drug-like DNA-encoded library.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Organic letters - 26(2024), 11 vom: 22. März, Seite 2212-2217 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Yue [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 25.03.2024 Date Revised 25.03.2024 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.orglett.4c00377 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM369418883 |
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| 500 | |a Citation Status MEDLINE | ||
| 520 | |a In this report, we present a photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif coupled with a Reversible Adsorption to Solid Support (RASS) strategy. A variety of valuable DNA-encoded seven-membered ring compounds, including DNA-encoded 3H-azepines, azepinones, and unnatural amino acids, are now accessible. Crucially, this DNA-compatible protocol can also be applied for the introduction of complex molecules, as exemplified by Lorcaserin and Betahistine. The selective conversion of readily available phenyl rings into high-value seven-membered rings offers a promising avenue for the construction of diversified and drug-like DNA-encoded library | ||
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| 700 | 1 | |a Xiao, Wen-Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Lv, Jing-Yi |e verfasserin |4 aut | |
| 700 | 1 | |a Shi, Wen-Xia |e verfasserin |4 aut | |
| 700 | 1 | |a Zou, Yong |e verfasserin |4 aut | |
| 700 | 1 | |a Yan, Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xue-Jing |e verfasserin |4 aut | |
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