A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3, 4-dihydroisoquinolines

…, EG Corley, P Davis, EJJ Grabowski…

文献索引：Larsen, Robert D.; Reamer, Robert A.; Corley, Edward G.; Davis, Paul; Grabowski, Edward J. J.; et al. Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6034 - 6038

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被引用次数: 82

摘要

A modification of the Bischler-Napierahki reaction for the cyclization of (1, 2-diphenylethyl) amides to the 3-aryl-3, 4-dihydroi~ oquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by ita conversion to an N-acyliminium intermediate with oxalyl chloride-FeCla. Removal of the oxalyl group in refluxing MeOH- sulfuric acid provides the 3, 4-dihydroisoquinolines in moderate to high yields. The ...