Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines

被引：35

作者：

Fuchs, JR ^{[1
]}

Funk, RL ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 21期

关键词：

D O I：

10.1021/ol016592n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

引用

页码：3349 / 3351

页数：3

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