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Keywords = orthoquinol imines

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11 pages, 2368 KiB  
Article
Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions
by Itaru Nakamura, Mai Tachibana, Riku Konta, Hiroki Tashiro and Masahiro Terada
Molecules 2023, 28(10), 4251; https://doi.org/10.3390/molecules28104251 - 22 May 2023
Cited by 2 | Viewed by 2914
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Advances on the Application of N-O Bond Compounds)
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16 pages, 291 KiB  
Article
Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation
by S. Quideau, L. Pouységu, A. Ozanne and J. Gagnepain
Molecules 2005, 10(1), 201-216; https://doi.org/10.3390/10010201 - 31 Jan 2005
Cited by 50 | Viewed by 14314
Abstract
Treatment of 2-methylphenols with chloro(diphenyl)-λ3-iodane led to theirregioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via aproposed ligand coupling reaction. In the same vein of investigation, treatment of2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to theirregioselective dearomatization into previously undescribed ortho-quinol imines. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
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