Catalyst-free and atom-economical [4+3] cycloaddition of azadienes with cyclic azomethine imines for facile synthesis of 1,2,4-triazepines

Li, Lesong; Liu, Tao; Ren, Weiwu; Wang, Yang

doi:10.1016/j.gresc.2022.10.010

Cited by 5 publications

(1 citation statement)

References 29 publications

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“…In order to achieve this reaction, the following challenges need to be solved: (1) the linear/branched regioselectivity of π-allyl all-carbon 1,6-dipoles; (2) the C/N site regioselectivity of azadiene dipolarophiles. 8–11 With this in mind, we designed and synthesized a novel all-carbon 1,6-dipole precursor, which can be used in the [6 + 4] cycloaddition reaction to synthesize ten-membered heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

Chen,

Lin,

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

Chen,

Lin,

et al. 2024

Org. Chem. Front.

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Lewis Base Controlled (4+3) and (4+2) Annulations of MBH Carbonates with Benzofuran‐Derived Azadienes: Access to Highly Substituted Benzofuro[3,2‐b]Azepines and Spirotetrahydroquinolines

Wang,

Li,

et al. 2024

Adv Synth Catal

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Catalyst‐controlled switchable (4 + 3) and (4 + 2) annulation reactions of Morita–Baylis–Hillman carbonates with benzofuran‐derived azadienes have been established. Employing PCy3 as the catalyst, the reaction could provide a variety of synthetically useful benzofuro[3,2‐b]azepines in good yields (80‐92%) with excellent chemo‐ and regioselectivities via (4 + 3) cycloaddition reactions. Whereas changing the catalyst from PCy3 to DMAP, the chemo‐ and regioselectivities were switched to construct highly substituted spirotetrahydroquinoline scaffolds with three sequential stereocenters containing all‐carbon spiro‐quaternary stereocenters in excellent efficiency and diastereoselectivities (92‐96% yields with all cases > 25:1 dr) via (4 + 2) annulations. In addition, the synthetic utility of this method was further showcased by gram‐scale reactions and synthetic transformations of the product.

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Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates

Lu,

Wang,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryWe report a palladium‐catalyzed asymmetric [4+4] cycloaddition reaction between 2‐alkylidenetrimethylene carbonate and electron‐deficient indole‐2,3‐quinodimethanes (IQDMs). This reaction features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity (up to 95% ee), and easy scale‐up without any loss of efficiency, making it valuable for the synthesis of indole‐fused eight‐membered oxa‐rings.

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Catalyst-free and atom-economical [4+3] cycloaddition of azadienes with cyclic azomethine imines for facile synthesis of 1,2,4-triazepines

Cited by 5 publications

References 29 publications

Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles

Lewis Base Controlled (4+3) and (4+2) Annulations of MBH Carbonates with Benzofuran‐Derived Azadienes: Access to Highly Substituted Benzofuro[3,2‐b]Azepines and Spirotetrahydroquinolines

Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates

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