Next Article in Journal
Evaluation of the Chemical Composition of Brazilian Commercial Cymbopogon citratus (D.C.) Stapf Samples
Previous Article in Journal
Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
Article Menu

Export Article

Open AccessArticle
Molecules 2008, 13(8), 1846-1863; doi:10.3390/molecules13081846

Oligomerization of Indole Derivatives with Incorporation of Thiols

Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical center, Uppsala University, S-751 24, Uppsala, Sweden
Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia
Department of Biochemistry and Organic Chemistry, Box 576, Uppsala University, S-751 23, Uppsala, Sweden
Author to whom correspondence should be addressed.
Received: 10 June 2008 / Revised: 18 August 2008 / Accepted: 19 August 2008 / Published: 26 August 2008
View Full-Text   |   Download PDF [424 KB, uploaded 18 June 2014]   |  


Two molecules of indole derivative, e.g. indole-5-carboxylic acid, reacted with one molecule of thiol, e.g. 1,2-ethanedithiol, in the presence of trifluoroacetic acid to yield adducts such as 3-[2-(2-amino-5-carboxyphenyl)-1-(2-mercaptoethylthio)ethyl]-1Hindole-5-carboxylic acid. Parallel formation of dimers, such as 2,3-dihydro-1H,1'H-2,3'-biindole-5,5'-dicarboxylic acid and trimers, such as 3,3'-[2-(2-amino-5-carboxyphenyl) ethane-1,1-diyl]bis(1H-indole-5-carboxylic acid) of the indole derivatives was also observed. Reaction of a mixture of indole and indole-5-carboxylic acid with 2-phenylethanethiol proceeded in a regioselective way, affording 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H-indole-5-carboxylic acid. An additional product of this reaction was 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-2,3-dihydro-1H,1'H-2,3'-biindole-5'-carboxylic acid, which upon standing in DMSO-d6 solution gave 3-[2-(2-aminophenyl)-1-(phenethylthio)ethyl]-1H,1'H-2,3'-biindole-5'-carboxylic acid. Structures of all compounds were elucidated by NMR, and a mechanism for their formation was suggested. View Full-Text
Keywords: Side reaction; oligomerization of indole derivatives; incorporation of thiols; regioselectivity; NMR study Side reaction; oligomerization of indole derivatives; incorporation of thiols; regioselectivity; NMR study

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Mutulis, F.; Gogoll, A.; Mutule, I.; Yahorava, S.; Yahorau, A.; Liepinsh, E.; Wikberg, J.E. Oligomerization of Indole Derivatives with Incorporation of Thiols. Molecules 2008, 13, 1846-1863.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top