29076-94-6Relevant academic research and scientific papers
A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines
Larsen, Robert D.,Reamer, Robert A.,Corley, Edward G.,Davis, Paul,Grabowski, Edward J. J.,et al.
, p. 6034 - 6038 (1991)
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.
