[8+3]-Cycloaddition of Tropones with Azaoxyallyl Cations.
1,4-oxazinones
[8+3] cycloaddition
azaoxyallyl cations
heterocycles
tropones
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
13 Dec 2019
13 Dec 2019
Historique:
received:
26
08
2019
revised:
17
09
2019
pubmed:
19
9
2019
medline:
19
9
2019
entrez:
19
9
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 31529771
doi: 10.1002/asia.201901198
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4748-4753Subventions
Organisme : Science and Engineering Research Board
ID : File Number: EMR/2016/007021
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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CCDC 1949335 and 1949337 (3 c and 3 i) contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.
The tropone derivatives decomposed under the reaction conditions. The side products formed were not characterized.
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