The Gassman indole synthesis is a set of chemical reactions which are used to synthesize substituted indoles by aniline.
This is a one-pot chemical reaction, and any of the intermediates are not isolated. R1 can be hydrogen or alkyl, whereas R2 works best with aryl, but can be alkyl as well. Electron-rich anilines, like 4-methoxyaniline, tend to be unsuccessful in this reaction.
The 3-position thiomethyl group is sometimes removed using Raney nickel to yield the 3-H-indole.
Mechanism of Reaction
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