Journal of Organic Chemistry p. 6034 - 6038 (1991)
Update date:2022-09-26
Topics:
Larsen, Robert D.
Reamer, Robert A.
Corley, Edward G.
Davis, Paul
Grabowski, Edward J. J.
et al.
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.
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