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

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-...

Descripción completa

Detalles Bibliográficos
Autores principales: Mutulis, Felikss, Erdélyi, Máté, Mutule, Ilze, Kreicberga, Jana, Yahorava, Sviatlana, Yahorau, Aleh, Borisova-Jan, Larisa, Wikberg, Jarl E.S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2003
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146916/
http://dx.doi.org/10.3390/81000728
_version_ 1783356484113924096
author Mutulis, Felikss
Erdélyi, Máté
Mutule, Ilze
Kreicberga, Jana
Yahorava, Sviatlana
Yahorau, Aleh
Borisova-Jan, Larisa
Wikberg, Jarl E.S.
author_facet Mutulis, Felikss
Erdélyi, Máté
Mutule, Ilze
Kreicberga, Jana
Yahorava, Sviatlana
Yahorau, Aleh
Borisova-Jan, Larisa
Wikberg, Jarl E.S.
author_sort Mutulis, Felikss
collection PubMed
description 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 (1)H- and (13)C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %).
format Online
Article
Text
id pubmed-6146916
institution National Center for Biotechnology Information
language English
publishDate 2003
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61469162018-11-19 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study Mutulis, Felikss Erdélyi, Máté Mutule, Ilze Kreicberga, Jana Yahorava, Sviatlana Yahorau, Aleh Borisova-Jan, Larisa Wikberg, Jarl E.S. Molecules Article 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 (1)H- and (13)C-NMR spectra. The side reaction could be suppressed by the use of 1,2-ethanedithiol in high concentrations (16 %). MDPI 2003-10-31 /pmc/articles/PMC6146916/ http://dx.doi.org/10.3390/81000728 Text en © 2003 (http://www.mdpi.org). Reproduction is permitted for non-commercial purposes.
spellingShingle Article
Mutulis, Felikss
Erdélyi, Máté
Mutule, Ilze
Kreicberga, Jana
Yahorava, Sviatlana
Yahorau, Aleh
Borisova-Jan, Larisa
Wikberg, Jarl E.S.
2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title_full 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title_fullStr 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title_full_unstemmed 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title_short 2-(p-Hydroxybenzyl)indoles - Side Products Formed Upon Cleavage of Indole Derivatives from Carboxylated Wang Polymer - an NMR Study
title_sort 2-(p-hydroxybenzyl)indoles - side products formed upon cleavage of indole derivatives from carboxylated wang polymer - an nmr study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146916/
http://dx.doi.org/10.3390/81000728
work_keys_str_mv AT mutulisfelikss 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT erdelyimate 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT mutuleilze 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT kreicbergajana 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT yahoravasviatlana 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT yahoraualeh 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT borisovajanlarisa 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy
AT wikbergjarles 2phydroxybenzylindolessideproductsformeduponcleavageofindolederivativesfromcarboxylatedwangpolymerannmrstudy

Ejemplares similares