Bischler-Napieralski reaction
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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.
[edit] References
- August Bischler, Bernard Napieralski (1893). "Zur Kenntniss einer neuen Isochinolinsynthese". Berichte der Deutschen Chemischen Gesellschaft 26 (2): 1903. doi:.
- Whaley, W.M.; Govindachari, T.R. Org. React. 1951, 6, 74. (Review)
- Bergstrom, F. W. Chem. Rev. 1944, 35, 218. (Review)
- Gábor Fodor, J. Gal, B. A. Phillips (1972). "The Mechanism of the Bischler-Napieralski Reaction". Angewandte Chemie International Edition in English 11 (10): 919–920. doi:.
[edit] See also
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