Synthesis of meta-Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement—Oxa-Michael Addition Cascade Reactions-Reference-Cited by-同舟云学术

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

Published:2023-05-22 Issue:10 Volume:28 Page:4251
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Nakamura Itaru¹^ORCID,Tachibana Mai²,Konta Riku²,Tashiro Hiroki²,Terada Masahiro²

Affiliation:

1. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

2. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

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.

Funder

JSPS KAKENHI

MEXT, Japan

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/10/4251/pdf

Reference36 articles.

1. SEA0400, a Novel and Selective Inhibitor of the Na+-Ca2+ Exchanger, Attenuates Reperfusion Injury in the In Vitro and In Vivo Cerebral Ischemic Models;Matsuda;J. Pharmacol. Exp. Ther.,2001

2. Tetrapetalone A, a novel lipoxygenase inhibitor from Streptomyces sp.;Komoda;Tetrahedron Lett.,2003

3. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors;Kamal;Nature,2003

4. Discovery of meta-Amido Bromophenols as New Antitubercular Agents;Liang;Chem. Pharm. Bull.,2019

5. Synthesis and Cytotoxicity against Human Breast Carcinoma Cell Evaluation of Some New 3,4-Disubstituted Coumarin Derivatives;Radwan;Pharm. Chem. J.,2022

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