One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles

被引：177

作者：

Manning, James R. ^{[1
]}

Davies, Huw M. L. ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 27期

关键词：

D O I：

10.1021/ja803139k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-hydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general with a range of carbenoid and isoxazole components and represents a unique disconnection strategy for the synthesis of functionalized pyridines.

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页码：8602 / +

页数：3

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