Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 14, Issue 24, Pages 4748-4753Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201901198
Keywords
[8+3] cycloaddition; 1; 4-oxazinones; azaoxyallyl cations; heterocycles; tropones
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Funding
- Science and Engineering Research Board [File Number: EMR/2016/007021] Funding Source: Medline
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Although azaoxyallyl cations are widely used as 1,3-dipoles for various cycloaddition reactions leading to nitrogen-containing heterocycles, their application in higher-order cycloaddition reaction remains scarce. Herein, we present the [8+3]-cycloaddition reaction of tropones with in situ generated azaoxyallyl cations allowing the one-step construction of cycloheptatriene-fused 1,4-oxazinones in moderate to good yields. This base-promoted new carbon-oxygen and carbon-nitrogen bond-forming reaction takes place under mild conditions in the absence of transition metal catalysts.
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