TBAI-Catalysed Formal [4+4]-Cycloaddition : Easy Access to Oxa-Bridged Eight-Membered Heterocycles
© 2023 Wiley-VCH GmbH..
TBAI-catalysed [4+4]-cyclization reaction of anthranils with hydrazones to deliver oxa-bridged eight-membered heterocycles in accepted yields was developed. Preliminary mechanistic studies indicated that the reaction involved the in situ generation of vinyldiazenes from readily available hydrazones followed by an aza-Michael addition of the anthranil substrates onto the vinyldiazenes and subsequent annulation. This transformation involved the formation of two new C-N bonds and C-O bond in one pot, overcoming the synthetic limitations of anthranils in organic chemistry. This strategy benefits from high efficiency and atomic economy with mild reaction conditions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
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| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 29(2023), 25 vom: 02. Mai, Seite e202300301 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wang, Wenxiang [VerfasserIn] |
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| Links: |
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| Themen: |
Anthranils |
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| Anmerkungen: |
Date Completed 03.05.2023 Date Revised 04.05.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chem.202300301 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a TBAI-catalysed [4+4]-cyclization reaction of anthranils with hydrazones to deliver oxa-bridged eight-membered heterocycles in accepted yields was developed. Preliminary mechanistic studies indicated that the reaction involved the in situ generation of vinyldiazenes from readily available hydrazones followed by an aza-Michael addition of the anthranil substrates onto the vinyldiazenes and subsequent annulation. This transformation involved the formation of two new C-N bonds and C-O bond in one pot, overcoming the synthetic limitations of anthranils in organic chemistry. This strategy benefits from high efficiency and atomic economy with mild reaction conditions | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a TBAI-catalyzed | |
| 650 | 4 | |a anthranils | |
| 650 | 4 | |a high efficiency and atom economy | |
| 650 | 4 | |a intermolecular formal [4+4]-cycloaddition | |
| 650 | 4 | |a oxa-bridged eight-membered heterocycles | |
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| 700 | 1 | |a Cui, Xiuling |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Yangjie |e verfasserin |4 aut | |
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