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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 21期

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.

引用

页码：6034 / 6038

页数：5

共 52 条

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