Povarov Reactions Involving 3-Aminocoumarins: Synthesis of 1,2,3,4-Tetrahydropyrido[2,3-c]coumarins and Pyrido[2,3-c]coumarins

被引：80

作者：

Kudale, Amit A. ^{[1
]}

Kendall, Jamie ^{[1
]}

Miller, David O. ^{[2
]}

Collins, Julie L. ^{[2
]}

Bodwell, Graham J. ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

[2] Mem Univ Newfoundland, CREAIT Network, St John, NF A1C 5S7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 21期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1021/jo801411p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 3-aminocoumarin (5) with 4-nitrobenzaldehyde (8) afforded a 2-azadiene (9), which reacted with various electron-rich alkenes (10 examples) in the presence of Yb(OTf)(3) to afford 1,2,3,4-tetrahydropyrido[2,3-c]coumarins. Yields were generally good, but the diastereomeric ratios were highly variable. The products arose through a formal [4 + 2] cycloaddition (inverse electron demand Diels-Alder reaction) followed by tautomerization. As such, these are examples of the Povarov reaction. A range of 1,2,3,4-tetrahydropyrido[2,3-c]coumarins was then synthesized using a three-component version of this reaction, which involves in situ formation of the 2-azadiene component. Some of these products were converted into the corresponding pyrido[2,3-c]coumarins upon treatment with various oxidants, the most effective of which proved to be nitrous gases.

引用

页码：8437 / 8447

页数：11

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