Catalyst-free inverse-electron-demand aza-Diels–Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Yang, Dezhi; Zhu, Meng; Wang, Taimin; He, Yixuan; Xie, Liang; Zhang, Jiayong; Cheng, Bin

doi:10.1039/d3ob00511a

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00511a

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Catalyst-free inverse-electron-demand aza-Diels–Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Dezhi Yang

Meng Zhu

Taimin Wang

et al.

Abstract: An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free, additive-free conditions was developed, which provided a highly convenient and straightforward method to construct a series of polyfunctionalized tetrahydropyridines in...

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2024

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Cited by 3 publications

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Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

Zhang,

Wang,

Chen

et al. 2024

J. Org. Chem.

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Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium and oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range of hexahydropyrimidine and 1,3oxazinane derivatives in good to excellent yields (up to 99%). The acyclic sulfonamido-substituted allylic carbonates as aza-πallylpalladium 1,4-dipole precursors also apply to the developed synthesized strategy, achieving the synthesis of hexahydropyrimidines. Moreover, the in situ-generated aza-π-allylpalladium 1,4dipoles undergoing dimeric [4 + 4] cycloaddition were also demonstrated by the construction of 1,5-diazocane derivatives.

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Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

Zhang,

Wang,

Chen

et al. 2024

J. Org. Chem.

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B(C₆F₅)₃/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes

Liu,

Qian,

Chen

et al. 2024

Org. Lett.

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Herein, we report an asymmetric aza-Diels−Alder reaction of quinoxalinones or benzoxazinones with unactivated dienes by utilizing a B(C 6 F 5 ) 3 /chiral phosphoric acid catalyst to construct chiral six-membered N-heterocycles. Various quinoxalinones or benzoxazinones with electron-withdrawing and electron-donating groups and unactivated dienes were tolerated (up to 99% yield and 99% ee) in the methodology with only 2 mol % catalyst loading. Moreover, the luminescence mechanism and photophysical properties of the product were tested and used for anticounterfeiting of QR codes.

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Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

Liu,

Li,

Huang

et al. 2024

Org. Chem. Front.

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Catalyst-free inverse-electron-demand aza-Diels–Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Cited by 3 publications

References 88 publications

Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

B(C₆F₅)₃/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes

Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

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Catalyst-free inverse-electron-demand aza-Diels–Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Cited by 3 publications

References 88 publications

Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes

B(C6F5)3/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes

Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

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Product

Resources

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B(C₆F₅)₃/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes