Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-estersElectronic supplementary information (ESI) available: Experimental procedures, spectral and analytical data (PDF) and X-ray crystallographic analyses of SG-HQ1 (3f), 3b, and 4b (CIF). CCDC 1548392-1548394. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ra05287a

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 wer...

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Bibliographic Details
Main Authors Park, Yongseok, Fei, Xiang, Yuan, Yue, Lee, Sanha, Hur, Joonseong, Park, Sung Jean, Jung, Jae-Kyung, Seo, Seung-Yong
Format Journal Article
LanguageEnglish
Published 30.08.2017
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Summary: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. Chemoselective controls in acylation of 2-amino-8-quinolinol.
Bibliography:For ESI and crystallographic data in CIF or other electronic format see DOI
3f
1548392-1548394
Electronic supplementary information (ESI) available: Experimental procedures, spectral and analytical data (PDF) and X-ray crystallographic analyses of
and
(
)
(CIF). CCDC
4b
10.1039/c7ra05287a
SG-HQ1
3b
ISSN:2046-2069
DOI:10.1039/c7ra05287a