NDLI: Synthesis of <i>meta</i>-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement-Oxa-Michael Addition Cascade Reactions.

Content Provider	Europe PMC
Author	Nakamura, Itaru Tachibana, Mai Konta, Riku Tashiro, Hiroki Terada, Masahiro
Editor	Mo, Dongliang Wei, Ye
Copyright Year	2023
Abstract	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.
Journal	Molecules
Volume Number	28
DOI	10.3390/molecules28104251
PubMed Central reference number	PMC10221852
Issue Number	10
PubMed reference number	37241991
e-ISSN	14203049
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2023-05-22
Access Restriction	Open
Subject Keyword	anilines cascade reaction rearrangement copper catalysts
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry

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Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement-Oxa-Michael Addition Cascade Reactions.