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2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study

Author(s): Felikss Mutulis | Máté Erdélyi | Ilze Mutule | Jana Kreicberga | Sviatlana Yahorava | Aleh Yahorau | Larisa Borisova-Jan | Jarl E.S. Wikberg

Journal: Molecules
ISSN 1420-3049

Volume: 8;
Issue: 10;
Start page: 728;
Date: 2003;
Original page

Keywords: Carboxylated Wang polymer | side reaction | p-hydroxybenzylation | 1 | 2-ethanedithiol | NMR

Treatment of carboxylated Wang polymer attached to a 2-unsubstituted indole derivative with a trifluoroacetic acid based mixture resulted in a side reaction: p-hydroxybenzylation at the 2-position of the indole ring. The structure of the resulting N-3-aminopropyl)-N-benzyl-4-[2-(4-hydroxybenzyl)-1H-indol-3-yl]-butyramide trifluoroacetate was ascertained by a full assignment of its 1H- and 13C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %).
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