A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

Robert D. Larsen, Robert A. Reamer, Edward G. Corley, Paul Davis, Edward J.J. Grabowski, Paul J. Reider, Ichiro Shinkai

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Abstract

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

Original languageEnglish (US)
Pages (from-to)6034-6038
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number21
DOIs
StatePublished - Oct 1 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Larsen, R. D., Reamer, R. A., Corley, E. G., Davis, P., Grabowski, E. J. J., Reider, P. J., & Shinkai, I. (1991). A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines. Journal of Organic Chemistry, 56(21), 6034-6038. https://doi.org/10.1021/jo00021a014