Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement-Oxa-Michael Addition Cascade Reactions
Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF6 afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the nitrogen atom to the methyl-substituted ortho position, followed by an oxa-Michael reaction of the resulting ortho-quinol imine intermediate.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:28 |
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| Enthalten in: |
Molecules (Basel, Switzerland) - 28(2023), 10 vom: 22. Mai |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Nakamura, Itaru [VerfasserIn] |
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| Links: |
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| Themen: |
Anilines |
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| Anmerkungen: |
Date Completed 28.05.2023 Date Revised 30.05.2023 published: Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.3390/molecules28104251 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM357442180 |
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| 500 | |a Date Revised 30.05.2023 | ||
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF6 afforded the corresponding meta-aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the nitrogen atom to the methyl-substituted ortho position, followed by an oxa-Michael reaction of the resulting ortho-quinol imine intermediate | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Konta, Riku |e verfasserin |4 aut | |
| 700 | 1 | |a Tashiro, Hiroki |e verfasserin |4 aut | |
| 700 | 1 | |a Terada, Masahiro |e verfasserin |4 aut | |
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