Oligomerization of Indole Derivatives with Incorporation of Thiols

Molecules

Felikss Mutulis¹  Adolf Gogoll²  Ilze Mutule¹  Sviatlana Yahorava¹  Aleh Yahorau¹  Edvards Liepinsh³ 

[1] Department of Pharmaceutical Biosciences, Division of Pharmaceutical Pharmacology, Uppsala Biomedical center, Uppsala University, S-751 24, Uppsala, Sweden; E-mails:;Department of Biochemistry and Organic Chemistry, Box 576, Uppsala University, S-751 23, Uppsala, Sweden; E-mail:;Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia; E-mail:

关键词: Side reaction;    oligomerization of indole derivatives;    incorporation of thiols;    regioselectivity;    NMR study;   

DOI  :  10.3390/molecules13081846

来源: mdpi

【 摘 要 】

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]-1H-indole-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-carboxy-phenyl)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.

【 授权许可】

CC BY   
© 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.