Issue 67, 2017, Issue in Progress
From the journal:

RSC Advances

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters†

Yongseok Park,‡a   Xiang Fei,‡a   Yue Yuan,a   Sanha Lee,a   Joonseong Hur,b   Sung Jean Park,a   Jae-Kyung Jung ORCID logo c  and  Seung-Yong Seo ORCID logo *a  

* Corresponding authors

a College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, South Korea

b College of Pharmacy, Seoul National University, Seoul 08826, South Korea

c College of Pharmacy, Chungbuk National University, Cheongju, Chungbuk 28644, South Korea

Abstract

Two different ways to carry out the chemoselective acylation of 2-amino-8-quinolinol with unique features to generate C2-amides or C8-esters were developed. The coupling reaction with a variety of carboxylic acids using EDCI and DMAP provided C8-ester derivatives, whereas N-heteroaromatic acids were not introduced on the C8-hydroxy group, but rather on the C2-amino group under the same conditions. To obtain C2-amides selectively, the anionic nucleophile from 2-amino-8-quinolinol was treated with less reactive acyl imidazolides or esters.

Graphical abstract: Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

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Article information

DOI
https://doi.org/10.1039/C7RA05287A
Article type
Paper
Submitted
10 May 2017
Accepted
23 Aug 2017
First published
30 Aug 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 41955-41961

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Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Y. Park, X. Fei, Y. Yuan, S. Lee, J. Hur, S. J. Park, J. Jung and S. Seo, RSC Adv., 2017, 7, 41955 DOI: 10.1039/C7RA05287A

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