Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent， Safety of Indole-5-carbonitrile, Which mentioned a new discovery about 15861-24-2
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-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.
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Reference：
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles