Studies on the reactivity of aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone: Reactions with amines

被引：23

作者：

Malamidou-Xenikaki, E ^{[1
]}

Spyroudis, S ^{[1
]}

Tsanakopoulou, M ^{[1
]}

机构：

[1] Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo0343679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone react with amines in refluxing dichloromethane to afford good yields of indanedione 2-carboxamides 5, through a ring-contraction and alpha,alpha'-dioxoketene formation reaction. These amides exist in solution in an unusual enol-amide form. In contrast, the same reactants in a copper-catalyzed reaction afford arylamines and 3-iodo-4-hydroxy-1,2-naphthoquinone.

引用

页码：5627 / 5631

页数：5

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