A Base‐Mediated Approach Towards Dihydrofuro[2,3‐<i>b</i>]Benzofurans from 2‐Nitrobenzofurans and 1,3‐Dicarbonyls

Singh, Gurdeep; Pandey, Rajat; Kurup, Adarsh S.; Anand, Ramasamy Vijaya

doi:10.1002/asia.202100184

Cited by 4 publications

(1 citation statement)

References 42 publications

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“…Singh et al described a straightforward one-pot synthesis of trifluoromethylated dihydrofuro [2,3-b]benzofurans 637 through a base-mediated Michael addition of ethyl 4,4,4-trifluoro-3oxobutanoate 1 to 2-nitrobenzofurans 636 followed by intramolecular cyclization (Scheme 225). [331] The scope of the reaction was extended to differently substituted 2nitrobenzo[b]furans 636, and products 637 were obtained in 43-71 % yields.…”

Section: Other Fused and Bridgehead Heterocyclesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Section: Other Fused and Bridgehead Heterocyclesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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A base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins: A simple and direct synthesis of dihydrofurobenzofuran-coumarins

Zhou

Mei

et al. 2023

Tetrahedron

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Au(PPh₃)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of cis-3a,8a-Dihydrofuro[2,3-b]benzofuran Framework

Zhang,

Deng

2024

J. Org. Chem.

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In the Au(PPh 3 )Cl/AgOTf/TsOH/MeCN/N 2 /25 °C system, diastereoselective synthesis of cis-3a,8a-dihydrofuro-[2,3-b]benzofuran derivatives with a substituent at the 8a-position has been achieved by using 1-(2-hydroxyphenyl)-3-arylprop-2-yn-1-ols and β-oxoketones (amides, acid) as starting materials. The studies revealed that the acidity of methylene in substrates plays a key role in the differential reactions. A stronger acidity of the methylene is favorable in the desired conversion. The unique role of TsOH as an additive acid in the synthesis strategy has been rationalized. 2-Oxo-phosphonate, 2-oxo-sulfonate, and 3-oxobutanoate are suitable for the conversion.

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A Base‐Mediated Approach Towards Dihydrofuro[2,3‐b]Benzofurans from 2‐Nitrobenzofurans and 1,3‐Dicarbonyls

Cited by 4 publications

References 42 publications

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

A base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins: A simple and direct synthesis of dihydrofurobenzofuran-coumarins

Au(PPh₃)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of cis-3a,8a-Dihydrofuro[2,3-b]benzofuran Framework

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A Base‐Mediated Approach Towards Dihydrofuro[2,3‐b]Benzofurans from 2‐Nitrobenzofurans and 1,3‐Dicarbonyls

Cited by 4 publications

References 42 publications

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

A base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins: A simple and direct synthesis of dihydrofurobenzofuran-coumarins

Au(PPh3)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of cis-3a,8a-Dihydrofuro[2,3-b]benzofuran Framework

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Au(PPh₃)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of cis-3a,8a-Dihydrofuro[2,3-b]benzofuran Framework