A MODIFIED BISCHLER-NAPIERALSKI PROCEDURE FOR THE SYNTHESIS OF 3-ARYL-3,4-DIHYDROISOQUINOLINES

被引:101
作者
LARSEN, RD
REAMER, RA
CORLEY, EG
DAVIS, P
GRABOWSKI, EJJ
REIDER, PJ
SHINKAI, I
机构
[1] Department of Process Research, Merck Sharp & Bohme Research Laboratories, Division of Merck & Co., Inc., Rahway, New Jersey 07065
关键词
D O I
10.1021/jo00021a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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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页码:6034 / 6038
页数:5
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