BF<sub>3</sub>·OEt<sub>2</sub> Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives

Wang, Yafei; Wang, Yujia; Qu, Jiaxin; Yang, Tongtong; Zhang, Yining; Yuan, Chunhao; Guo, Hongchao; Wang, Chang

doi:10.1021/acs.joc.4c00742

J. Org. Chem.

2024

DOI: 10.1021/acs.joc.4c00742

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BF₃·OEt₂ Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives

Yafei Wang,

Yujia Wang,

Jiaxin Qu

et al.

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Cited by 2 publications

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Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

Rakaee,

Shiri,

Farajpour

et al. 2024

J. Org. Chem.

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A versatile and atom-economic three-component reaction between 3-cyano-4-styrylcoumarins, 1,3-indandione, and aliphatic alcohols is described for synthesizing diversely multifunctionalized benzocoumarins. This strategy allows facile access to various benzocoumarins bearing an amine and a substituted benzoyl scaffold under simple heating conditions. Readily available precursors, operational simplicity, acceptable functional group tolerance, and excellent yields are some highlighted advantages of this transformation.

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Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

Rakaee,

Shiri,

Farajpour

et al. 2024

J. Org. Chem.

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DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

Qu,

Yang,

Zhao

et al. 2024

Org. Lett.

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The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives with moderate to excellent yields. This approach represents the first Lewis base (LB)catalyzed ring-opening reaction of vinyl epoxides, simultaneously providing a rare oxygen-containing active intermediate in this field. The gram-scale preparation and facile derivatization of the cycloadduct highlight the significant synthetic potential of this strategy.

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BF₃·OEt₂ Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives

Cited by 2 publications

References 55 publications

Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

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BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives

Cited by 2 publications

References 55 publications

Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

Contact Info

Product

Resources

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BF₃·OEt₂ Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives