Hemetsberger indole synthesis
- 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. [Hemetsberger, H.; Knittel, D. "Monatsh. Chem." 1972, "103", 194.] ["Recent developments in indole ring synthesis-methodology and applications". Gribble, G. W. "J. Chem. Soc., Perkin Trans. 1" 2000, 1045-1075. (Review)]
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 [Gilchrist, T. L. "Aldrichimica Acta" 2001, 34, 51. (Review)] intermediates have been isolated. The mechanism is postulated to proceed via a nitrene intermediate. [Knittel, D. "Synthesis" 1985, 186-188.]
References
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