Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation

Anna, Anna; Chen, Zhaohang; Qiao, Hongwei; Gao, Juanhong; Zhu, Mengyao; Li, Chao

doi:10.1016/j.catcom.2021.106360

Cited by 3 publications

(2 citation statements)

References 26 publications

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“…Therefore, reaction with a suitable two-carbon π component results in the formation of a new five-membered nitrogen heterocycle 8 , i.e., a pyrrole, indole, or reduced version thereof. This reactivity has been developed across a wide spectrum of substrates: alkenes, ,, alkynes, enol ethers, furans, indoles, and even arene moieties . There have also been some unique approaches to pyrroles and indoles from unsaturated carbonyl species, alcoholic unsaturated carbonyl species, unsaturated 1-STs, and vinyl anilines .…”

Section: Introductionmentioning

confidence: 99%

“…This reactivity has been developed across a wide spectrum of substrates: alkenes, 11b , 11d , 12 alkynes, 13 enol ethers, 14 furans, 15 indoles, 16 and even arene moieties. 17 There have also been some unique approaches to pyrroles and indoles from unsaturated carbonyl species, 18 alcoholic unsaturated carbonyl species, 19 unsaturated 1-STs, 20 and vinyl anilines. 21 The versatility of 1-ST reactivity means that many reactions are possible that result in heterocycle formation by the inclusion of a nitrogen-containing tether 22 , 23 or by providing valuable access to substrates that can be converted into five-membered azaheterocycles in short order.…”

Section: Introductionmentioning

confidence: 99%

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Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N–H Bond Insertion and Cyclodehydration

Williams

Boyer

2022

J. Org. Chem.

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A modular synthesis of highly substituted 3azapyrroles has been developed using a three-step sequence comprising copper-catalyzed alkyne−azide cycloaddition (CuAAC), N−H bond insertion, and cyclodehydration. 1-Sulfonyl-1,2,3-triazoles (1-STs) can be accessed from common alkyne and sulfonyl azide building blocks by CuAAC using CuTC. Rhodium(II)-acetate-promoted 1-ST denitrogenation results in highly electrophilic rhodium azavinyl carbenes that, here, underwent insertion into the N−H bond of secondary α-aminoketones to form 1,2-aminoalkenes. These products were cyclized and dehydrated using BF 3 •OEt 2 into highly substituted 3-azapyrroles. The three steps (CuAAC, N−H bond insertion, and cyclodehydration) could be telescoped into a one-pot process. The method proved to be highly efficient and tolerated a wide range of substituents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N–H Bond Insertion and Cyclodehydration

Williams

Boyer

2022

J. Org. Chem.

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Palladium-Catalyzed Carbonylative Homocoupling of 2-Iodophenols for the Synthesis of Symmetrical Xanthones

Lokolkar

Bhanage

2023

Synlett

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Herein, we report the palladium catalysed carbonylative synthesis of symmetrical xanthones from functionalised 2-iodophenols in one pot manner. The protocol involves homocoupling of 2-iodophenols using Pd catalyst, Cs2CO3 as base with gaseous CO as C1 building block. The simple, ligand-free and additive free strategy provides moderate to good yields of symmetrical xanthones. The reaction was also examined with the combination of 2-hydroxy phenyl boronic acid as another coupling partner. Additionally, this protocol was extended for the synthesis of aryl and alkyl salicylate derivatives by varying the reaction conditions.

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Ionic Liquids Immobilized Synthesis of New Xanthenes Derivatives and their Antiproliferative, Molecular Docking, and Morphological Studies

Mohareb,

Ibrahim,

Al Farouk

et al. 2024

ACAMC

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Background:: Xanthenes and benzoxanthenesare are highly valuable compounds in organic chemistry and medicinal chemistry. Xanthene derivatives were found to have many applications in medicinal chemistry. Objective:: This work aims to explore the synthesis of xanthene derivatives with various substituents and find the possibility of their uses as anticancer agents. Method:: The basic starting compound through this work was the 2,3-dihydro-1H-xanthen-1-one (3), which was synthesized from the reaction of cyclohexan-1,3-dione and 2-hydroxybenzaldehyde. Compound 3 synthesized new thiophene, pyrimidine, isoxazole, and thiazole derivatives based on the xanthenes nucleus. Fused xanthene derivatives were obtained through further heterocyclization reactions. Multicomponent reactions expressed in this work were carried out in the presence of solvent catalyzed by Et3N and in solvent-free ionic liquid immobilized catalyst. Results:: Cytotoxicity for the newly synthesized compounds toward cancer cell lines was measured, and the results revealed that many compounds exhibited high inhibitions. Conclusion:: The antiproliferative activity of the synthesized compounds was studied on six selected cancer cell lines. The nature of the heterocyclic ring and the variations of substituted groups showed a high effect through the inhibitions of the tested compound.

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Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation

Cited by 3 publications

References 26 publications

Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N–H Bond Insertion and Cyclodehydration

Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N–H Bond Insertion and Cyclodehydration

Palladium-Catalyzed Carbonylative Homocoupling of 2-Iodophenols for the Synthesis of Symmetrical Xanthones

Ionic Liquids Immobilized Synthesis of New Xanthenes Derivatives and their Antiproliferative, Molecular Docking, and Morphological Studies

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