Intramolecular Pd(II)-catalyzed cyclization of propargylamides: Straightforward synthesis of 5-oxazolecarbaldehydes

被引：101

作者：

Beccalli, Egle M. ^{[1
,2
]}

Borsini, Elena ^{[1
]}

Broggini, Gianluigi ^{[1
]}

Palmisano, Giovanni ^{[1
]}

Sottocornola, Silvia ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

[2] Univ Milan, Fac Farm, Inst Chim Organ A Marchesini, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 12期

关键词：

D O I：

10.1021/jo800621n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.

引用

页码：4746 / 4749

页数：4

共 49 条

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