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

Research output: Contribution to journalArticlepeer-review

106 Scopus citations


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
Issue number21
StatePublished - Oct 1 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


Dive into the research topics of 'A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines'. Together they form a unique fingerprint.

Cite this