Synthesis of Imeta/I-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 AgSbF[sub.6] 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...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2023-05, Vol.28 (10)
Hauptverfasser:	Nakamura, Itaru, Tachibana, Mai, Konta, Riku, Tashiro, Hiroki, Terada, Masahiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Nitrobenzenes Nitrogen Oxalic acid Substitution reactions
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creator	Nakamura, Itaru Tachibana, Mai Konta, Riku Tashiro, Hiroki Terada, Masahiro
description	Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF[sub.6] 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.
doi_str_mv	10.3390/molecules28104251
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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.</description><subject>Nitrobenzenes</subject><subject>Nitrogen</subject><subject>Oxalic acid</subject><subject>Substitution reactions</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqVi81KAzEURoMoWH8ewF0ewLT5G-osh1GxCxHUnYhcMnc6VzKJTNLBduVD-IR9Eltw4dbV93E4h7ELJafGlHLWR49u5THpKyWtLtQBmyirpTDSlod__jE7SeldSq2sKiZs87QOucNEiceWL3rMMFuIqqcQPzoM0fNrHGiETCMmPhLweiVqyODXG2z4i7o0r-IRYRggLLHHkLdf3w-fIO7JdYCeV01DmWLgNSQHDfKd7PYgnbGjFnzC8989ZdPbm-f6TizB4xuFNuYBHOyjnlwM2NKOV_NClqXRc2v-HfwApLZfIg</recordid><startdate>20230501</startdate><enddate>20230501</enddate><creator>Nakamura, Itaru</creator><creator>Tachibana, Mai</creator><creator>Konta, Riku</creator><creator>Tashiro, Hiroki</creator><creator>Terada, Masahiro</creator><general>MDPI AG</general><scope/></search><sort><creationdate>20230501</creationdate><title>Synthesis of Imeta/I-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions</title><author>Nakamura, Itaru ; Tachibana, Mai ; Konta, Riku ; Tashiro, Hiroki ; Terada, Masahiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-gale_infotracacademiconefile_A7509932743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Nitrobenzenes</topic><topic>Nitrogen</topic><topic>Oxalic acid</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakamura, Itaru</creatorcontrib><creatorcontrib>Tachibana, Mai</creatorcontrib><creatorcontrib>Konta, Riku</creatorcontrib><creatorcontrib>Tashiro, Hiroki</creatorcontrib><creatorcontrib>Terada, Masahiro</creatorcontrib><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakamura, Itaru</au><au>Tachibana, Mai</au><au>Konta, Riku</au><au>Tashiro, Hiroki</au><au>Terada, Masahiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Imeta/I-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><date>2023-05-01</date><risdate>2023</risdate><volume>28</volume><issue>10</issue><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF[sub.6] 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.</abstract><pub>MDPI AG</pub><doi>10.3390/molecules28104251</doi></addata></record>
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source	MDPI - Multidisciplinary Digital Publishing Institute; DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; Free Full-Text Journals in Chemistry
subjects	Nitrobenzenes Nitrogen Oxalic acid Substitution reactions
title	Synthesis of Imeta/I-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions
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