Hemetsberger indole synthesis
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Template:Short description Template:Use dmy dates Template:Reactionbox The Hemetsberger indole synthesis (also called the Hemetsberger–Knittel synthesis) is a chemical reaction that thermally decomposes a 3-aryl-2-azido-propenoic ester into an indole-2-carboxylic ester.[1][2]
Yields are typically above 70%. However, this is not a popular reaction, due to the lack of stability and difficulty in synthesizing the starting material.
Reaction mechanism
The mechanism is unknown. However, azirine[3] intermediates have been isolated. The mechanism is postulated to proceed via a nitrene intermediate.[4]
References
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