For faster navigation, this Iframe is preloading the Wikiwand page for Hemetsberger indole synthesis.

Hemetsberger indole synthesis

Hemetsberger indole synthesis
Named after Helfried Hemetsberger
Reaction type Ring forming reaction

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]

The Hemetsberger indole synthesis
The Hemetsberger indole synthesis

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

  1. ^ Hemetsberger, H.; Knittel, D. (1972). "Synthese und Thermolyse von α-Azidoacrylestern". Monatshefte für Chemie. 103: 194–204. doi:10.1007/BF00912944. S2CID 91741917.
  2. ^ Gribble, G. W. (2000). "Recent developments in indole ring synthesis-methodology and applications". J. Chem. Soc., Perkin Trans. (7): 1045–1075. doi:10.1039/a909834h.
  3. ^ Gilchrist, T. L. (2001). "Activated 2H-Azirines as Dienophiles and Electrophiles" (PDF). Aldrichimica Acta. 34 (2): 51. Archived from the original (PDF) on 15 May 2013.
  4. ^ Knittel, D. (1985). "Verbesserte Synthese von α-Azidozimtsäure-estern und 2H-Azirinen". Synthesis. 1985 (2): 186–188. doi:10.1055/s-1985-31149.
{{bottomLinkPreText}} {{bottomLinkText}}
This page is based on a Wikipedia article written by contributors (read/edit).
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.
Cover photo is available under {{::mainImage.info.license.name || 'Unknown'}} license. Cover photo is available under {{::mainImage.info.license.name || 'Unknown'}} license. Credit: (see original file).
Hemetsberger indole synthesis
Listen to this article

This browser is not supported by Wikiwand :(
Wikiwand requires a browser with modern capabilities in order to provide you with the best reading experience.
Please download and use one of the following browsers:

✕
This article was just edited, click to reload
This article has been deleted on Wikipedia (Why?)

Back to homepage

Please click Add in the dialog above
Please click Allow in the top-left corner,
then click Install Now in the dialog
Please click Open in the download dialog,
then click Install
Please click the "Downloads" icon in the Safari toolbar, open the first download in the list,
then click Install
{{::$root.activation.text}}

Install Wikiwand

Install on Chrome Install on Firefox
Don't forget to rate us

Tell your friends about Wikiwand!

Gmail Facebook Twitter Link

Enjoying Wikiwand?

Tell your friends and spread the love:
Share on Gmail Share on Facebook Share on Twitter Share on Buffer

Our magic isn't perfect

You can help our automatic cover photo selection by reporting an unsuitable photo.

This photo is visually disturbing This photo is not a good choice

Thank you for helping!


Your input will affect cover photo selection, along with input from other users.

X

Get ready for Wikiwand 2.0 🎉! the new version arrives on September 1st! Don't want to wait?