Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1,3-Indanedione and 2-Arylidene-1,3-indanediones

Ding, Bangdong; Yechao, Jiang; Yu, Zhengkun; Ye, Rong; Sun, Jian; Yan, Chao‐Guo

doi:10.6023/cjoc201910016

Cited by 6 publications

(1 citation statement)

References 10 publications

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“…In 2020, Yan and co-workers described the base-promoted reaction of quinolinium salts 5 (2 equiv) with 1,3-indanedione to mainly render functionalized dihydropyrrolo[1,2- a ]quinolines 84 , in which one quinoline ring was opened and the other one was incorporated into the final compound ( Scheme 60 , eq 1). 96 On the other hand, the three-component reaction of quinolinium salts 5 , 1,3-indanedione and aromatic aldehydes 85 in the presence of trimethylamine afforded spiropyrroloquinolines 86 in good yields ( Scheme 60 , eq 2). Electron-withdrawing and electron-donating substituents were tolerated on the aldehyde as well as on the quinolinium salt.…”

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

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Dearomatization reactions have become fundamental chemical transformations in organic synthesis since they allow for the generation of three-dimensional complexity from two-dimensional precursors, bridging arene feedstocks with alicyclic structures. When those processes are applied to pyridines, quinolines, and isoquinolines, partially or fully saturated nitrogen heterocycles are formed, which are among the most significant structural components of pharmaceuticals and natural products. The inherent challenge of those transformations lies in the low reactivity of heteroaromatic substrates, which makes the dearomatization process thermodynamically unfavorable. Usually, connecting the dearomatization event to the irreversible formation of a strong C−C, C− H, or C−heteroatom bond compensates the energy required to disrupt the aromaticity. This aromaticity breakup normally results in a 1,2-or 1,4-functionalization of the heterocycle. Moreover, the combination of these dearomatization processes with subsequent transformations in tandem or stepwise protocols allows for multiple heterocycle functionalizations, giving access to complex molecular skeletons. The aim of this review, which covers the period from 2016 to 2022, is to update the state of the art of nucleophilic dearomatizations of pyridines, quinolines, and isoquinolines, showing the extraordinary ability of the dearomative methodology in organic synthesis and indicating their limitations and future trends.

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Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

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Bifunctional Squaramide‐Catalyzed Asymmetric [3+2] Annluation Reactions of 2‐Isothiocyanato‐1‐indanones with 2‐Arylidene‐1,3‐indanediones

Zhai

Xie

2022

ChemistrySelect

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A squaramide-catalyzed asymmetric Michael/cyclization tandem reaction between 2-isothiocyanato-1-indanones and 2arylidene-1,3-indanediones was developed. Under this strategy, the corresponding chiral bispirocyclic indanone compounds containing two contiguous stereocenters were obtained under mild conditions in moderate to excellent yields (up to 99 %) and enantioselectivities (up to 98 % ee). In addition, further transformation experiments were achieved through the oxidation and methylation reactions of the product, which also confirmed the synthetic practicality of this synthetic strategy.

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Crystal structure of aminoquinophthalones and relation to steepness of the absorption in the solid state

Matsumoto,

Hasegawa,

Akazome

et al. 2025

Dyes and Pigments

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Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1,3-Indanedione and 2-Arylidene-1,3-indanediones

Cited by 6 publications

References 10 publications

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Bifunctional Squaramide‐Catalyzed Asymmetric [3+2] Annluation Reactions of 2‐Isothiocyanato‐1‐indanones with 2‐Arylidene‐1,3‐indanediones

Crystal structure of aminoquinophthalones and relation to steepness of the absorption in the solid state

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