An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2019 Apr 3

PMID 30934862

Citations 2

Authors

Wengang Wu

Jun Yi

Huipeng Xu

Shuangjun Li

Rongxin Yuan

Affiliations

Soon will be listed here.

Abstract

The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C⁻H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C⁻N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.

Citing Articles

Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process.

Meng C, Niu H, Ning J, Wu W, Yi J Molecules. 2020; 25(3).

PMID: 32019185 PMC: 7037277. DOI: 10.3390/molecules25030602.

Synthesis of Elaborate Benzofuran-2-carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C-H Arylation and Transamidation Chemistry.

Oschmann M, Johansson Holm L, Pourghasemi-Lati M, Verho O Molecules. 2020; 25(2).

PMID: 31952313 PMC: 7024369. DOI: 10.3390/molecules25020361.

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