Base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

Zhang, You-Ya; Li, Lin; Ma, Ai‐Jun; Wang, Weifeng; Peng, Jin‐Bao

doi:10.1039/d2ob01903e

Cited by 7 publications

References 61 publications

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Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Deng,

Lang,

Peng

2024

Adv Synth Catal

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The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has now emerged as a vital tool to construct oxindoles bearing all carbon quaternary centers. However, most of these reactions proceed via carbometalation‐initiated 5‐exo‐trig cyclization followed by nucleophilic trapping of the resulting σ alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐endo‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65‐89% yields from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using Zn/TMSCl system.

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Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Deng,

Lang,

Peng

2024

Adv Synth Catal

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Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

Wang,

Chen,

Yang

et al. 2024

Chemistry A European J

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B(C₆F₅)₃‐Catalyzed Aza‐Friedel–Crafts Reaction of Indolizines with 2‐Aryl‐3H‐indol‐3‐ones

Liu

Zou

et al. 2023

Eur J Org Chem

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A Friedel–Crafts reaction of indolizines with 2‐aryl‐3H‐indol‐3‐ones catalyzed by B(C6F5)3 is described. This protocol gives access to indolizine derivatives that are valuable building blocks in synthetic and pharmaceutical chemistry. The reaction proceeds under mild conditions, affording various C2‐quaternary indolin‐3‐ones based on indolizine with high yields and regioselectivities. Moreover, the synthetic transformations of the target products were realized by N‐methylation and trifluoromethane sulfonation.

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Base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

Abstract: A base-promoted [4+2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters for the syntheses of multisubstituted 5,6-dihydroindolizines was developed. Using DBN as base, the reaction proceeds smoothly under mild conditions to...

Cited by 7 publications

References 61 publications

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

B(C₆F₅)₃‐Catalyzed Aza‐Friedel–Crafts Reaction of Indolizines with 2‐Aryl‐3H‐indol‐3‐ones

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Base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

Abstract: A base-promoted [4+2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters for the syntheses of multisubstituted 5,6-dihydroindolizines was developed. Using DBN as base, the reaction proceeds smoothly under mild conditions to...

Cited by 7 publications

References 61 publications

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

B(C6F5)3‐Catalyzed Aza‐Friedel–Crafts Reaction of Indolizines with 2‐Aryl‐3H‐indol‐3‐ones

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B(C₆F₅)₃‐Catalyzed Aza‐Friedel–Crafts Reaction of Indolizines with 2‐Aryl‐3H‐indol‐3‐ones