Masked 3-aminoindan-1-ones by a palladium-catalyzed three-component annulation reaction

被引：36

作者：

Arefalk, A ^{[1
]}

Larhed, M ^{[1
]}

Hallberg, A ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, BMC, SE-75123 Uppsala, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 03期

关键词：

D O I：

10.1021/jo048187q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new palladium(0)-catalyzed three-component reaction involving a set of salicylic aldehyde triflates, ethylene glycol vinyl ether, and various secondary nucleophilic amines has been developed. Through systematic optimization experiments using multivariate design, the conditions effecting robust and convenient one-pot generation of protected 3-aminoindan-1-ones were identified. A reaction route involving an initial internal Heck arylation of the hydroxyalkyl vinyl ether, iminium ion formation, and subsequent tandem cyclization is invoked to explain the selective formation of the isolated tertiary 3-aminoindan acetals. Hydrogenolysis of orthogonally blocked 3-aminoindan-1-ones delivered primary or secondary amines after 10-20 min of microwave heating.

引用

页码：938 / 942

页数：5

共 21 条

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