Hemetsberger indole synthesis

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]

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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, aziridine^[3] intermediates have been isolated. The mechanism is postulated to proceed via a nitrene intermediate.^[4]

References