One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones

Wang, Bingqiao; Zhang, Qiu; Luo, Juan; Zhang, Gan; Jiang, Wen; Tang, Qiang

doi:10.3390/molecules24112187

Cited by 15 publications

(7 citation statements)

References 43 publications

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“…And it was found that derivatives with aryl-and vinylic-substituted alkynes gave cyclization products in exceptional yields. [33] A one-pot reaction including Sonogashira coupling of dichlorophenols (21) phenylphosphine catalyst. [34] The general schematic representation of all the reactions mentioned above is shown in Figure 4.…”

Section: Chemistry Of Benzofuransmentioning

confidence: 99%

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Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Dwarakanath

Gaonkar

2022

Asian J Org Chem

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Out of the many heterocycles that exhibit pharmaceutical and therapeutic properties, benzofurans remain the most eye-catching to scientists ever since their discovery. From being present in natural products to synthetic analogs they show diverse biological properties which are used to treat various diseases. Interestingly, some of the benzofuran hybrids were docked against COVID-19 Main Protease and it showed appealing results. Apart from medicinal properties it also exhibits some non-drug applications. The structure activity relationship of benzofuran derivatives in many infections draws attention to the extent where drugs can be produced in a short time span which highlights their significance in medicinal chemistry. There are considerable reaction schemes to synthesize this moiety either simple one pot reactions or multistep. Here, we emphasize on the chemistry of benzofurans, synthesis and its derivatives in the recent years, some of which show notable anti-tumor, antifungal, anti-mycobacterial and anti-oxidant activities.

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Section: Chemistry Of Benzofuransmentioning

confidence: 99%

“…[19] Synthetic analogs of benzofuran scaffold have been synthesized and many drugs bearing this moiety are available in the market treating various diseases, a few of which are given in Figure 2. [20,21]…”

Section: Introductionmentioning

confidence: 99%

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Dwarakanath

Gaonkar

2022

Asian J Org Chem

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“…One-pot processes for the synthesis of benzo[b]furans from aryl-or alkylketones using nonprecious Fe and Cu catalysis have been described by Sutherland and co-workers in 2020 (Scheme 32B and C) [165]. Benzofurans are important scaffolds present in several bioactive compounds, such as balsaminone A (91, antipruritic activity), xylarianaphthol-1 (92, anticancer activity), and amiodarone (93, antiarrhythmic activity) (Scheme 32A) [166]. The method consists of a tandem, regioselective Fe(III)-catalyzed C-H halogenation, followed by an Fe or Cu-catalyzed O-arylation to access the benzo[b]furan derivatives in high yields.…”

Section: Iron-catalyzed C-h Activationmentioning

confidence: 99%

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Carvalho¹,

Miranda²,

Nunes³

et al. 2021

Beilstein J. Org. Chem.

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Several valuable biologically active molecules can be obtained through C–H activation processes. However, the use of expensive and not readily accessible catalysts complicates the process of pharmacological application of these compounds. A plausible way to overcome this issue is developing and using cheaper, more accessible, and equally effective catalysts. First-row transition (3d) metals have shown to be important catalysts in this matter. This review summarizes the use of 3d metal catalysts in C–H activation processes to obtain potentially (or proved) biologically active compounds.

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“…More often, basic conditions are employed to improve the reactivity of naphthol as double nucleophile, as, for instance, in the classical approach of the annulation of 2-naphthol with dihalo compounds [ 18 ]. However, the use of p -TSA [ 19 , 20 ] or of metal catalysis [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ] has also been pursued.…”

Section: Introductionmentioning

confidence: 99%

An Easy Access to Furan-Fused Polyheterocyclic Systems

et al. 2022

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Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition to the double bond, followed by, e.g., intramolecular replacement of the nitro group) with the possibility to exploit a conjugated system of double bonds within an electrocyclization process. Herein, nitrostilbenes are reacted with different aromatic enols provided by a double (carbon and oxygen) nucleophilicity, leading to novel, interesting naphthodihydrofurans. From these, as a viable application, aromatization and electrocyclization lead in turn to valuable polycondensed, fully aromatic O-heterocycles.

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One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones

Cited by 15 publications

References 43 publications

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

An Easy Access to Furan-Fused Polyheterocyclic Systems

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