Oligomerization of indole derivatives with incorporation of thiols
2008 (English)In: Molecules, ISSN 1420-3049, Vol. 13, no 8, 1846-63 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2008. Vol. 13, no 8, 1846-63 p.
Side reaction, oligomerization of indole derivatives, incorporation of thiols, regioselectivity, NMR study
IdentifiersURN: urn:nbn:se:uu:diva-104209DOI: 10.3390/molecules13081846ISI: 000258756300020PubMedID: 18794789OAI: oai:DiVA.org:uu-104209DiVA: diva2:219541