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Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters
- Park, Yongseok, Fei, Xiang, Yuan, Yue, Lee, Sanha, Hur, Joonseong, Park, Sung Jean, Jung, Jae-Kyung, Seo, Seung-Yong
- RSC advances 2017 v.7 no.67 pp. 41955-41961
- Lewis bases, acylation, carboxylic acids, chemoselectivity, esters
- 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.