2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR StudyAuthor(s): Felikss Mutulis | MÃƒÂ¡tÃƒÂ© ErdÃƒÂ©lyi | 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;
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 %).