Bischler-Napieralski reaction
- Bischler-Napieralski reaction
The Bischler-Napieralski reaction is a chemical reaction that dehydrates an N-acyl β-arylethyl amines into the corresponding heterocycle. The reaction is named after August Bischler and Bernard Napieralski, who discovered the reaction at the University of Zurich
With less nucleophilic aryl groups, more harsh conditions are required. Indoles react readily upon warming in benzene. Benzene rings require higher temperatures.
Phosphorus oxychloride is the most often used dehydrating agent. Phosphorus pentachloride, polyphosphoric acid, and zinc chloride have also proven successful.
References
* cite journal
author = August Bischler, Bernard Napieralski
journal =Berichte der Deutschen Chemischen Gesellschaft
title = Zur Kenntniss einer neuen Isochinolinsynthese
year = 1893
volume = 26
issue = 2
pages = 1903
doi = 10.1002/cber.189302602143
url = http://gallica.bnf.fr/ark:/12148/bpt6k90729g/f756.table
* Whaley, W.M.; Govindachari, T.R. "Org. React." 1951, "6", 74. (Review)
* Bergstrom, F. W. "Chem. Rev." 1944, "35", 218. (Review)
* cite journal
author = Gábor Fodor, J. Gal, B. A. Phillips
journal =Angewandte Chemie International Edition in English
title = The Mechanism of the Bischler-Napieralski Reaction
year = 1972
volume = 11
issue = 10
pages = 919–920
doi = 10.1002/anie.197209191
url =
ee also
*Pictet-Spengler reaction
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