Visible light promoted synthesis of dihydropyrano[2,3-c]chromenes via a multicomponent-tandem strategy under solvent and catalyst free conditions

Tiwari, Jyoti; Saquib, Mohammad; Tufail, Fatima; Singh, Manoj Kumar; Singh, Jaya; Singh, Jagdamba

doi:10.1039/c5gc02855h

Cited by 60 publications

(22 citation statements)

References 71 publications

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“…In accordance with previous literature reports , a plausible radical mechanism is proposed (Scheme ). It is proposed that the aldehydes undergo Norrish‐type cleavage and phenolic hydrogen of the 4‐hydroxycoumarin breaks symmetrically to form the radical.…”

Section: Resultssupporting

confidence: 87%

Visible Light‐Induced Synthesis of Biscoumarin Analogs under Catalyst‐Free Conditions

Nadaf

Shivashankar

2018

Journal of Heterocyclic Chem

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Section: Resultssupporting

confidence: 87%

Visible Light‐Induced Synthesis of Biscoumarin Analogs under Catalyst‐Free Conditions

Nadaf

Shivashankar

2018

Journal of Heterocyclic Chem

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“…Three‐component one‐pot reaction of 4‐hydroxycoumarin, 4‐fluorobenzaldehyde, and malononitrile in refluxing absolute ethanol in the presence of piperidine afforded the 2‐amino‐3‐cyanopyranocoumarin 23 that was reacted with trimethylorthoformate or triethylorthoformate to yield the corresponding tricyclic methoxymethylene amino or ethoxymethylene amino derivatives 24 and 25 , respectively. Cyclization of compound 25 with hydrazine hydrate gave the corresponding tetracyclic pyranopyrimidine derivative 26 .…”

Section: Resultsmentioning

confidence: 99%

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Batran

Dawood

Elseginy

et al. 2017

Archiv der Pharmazie

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Breast and cervical cancers are the most common gender-specific cancers affecting women worldwide. In this investigation, we highlighted the synthesis, VEGFR-2 and p38α MAPK inhibitory activity of new series of fluorinated coumarin-based derivatives featuring a variety of bioactive chemical moieties attached or fused to the coumarin nucleus at the 3 and/or 4 position. The bioactive inhibitors were further assessed for their anti-proliferative effect against human MCF-7 breast cancer and HeLa cervical cancer cell lines, respectively. Most of the tested compounds showed potent preferential inhibition effects against human VEGFR-2 and remarkable anticancer activities in the human breast cancer cell line MCF-7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR-2 (94% inhibition) and they were the most potent anticancer agents toward MCF-7 cancer cells with IC values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13 inhibited p38α MAPK phosphorylation with a significant reduction in % cell viability against HeLa cancer cells at 10 and 30 µM. Docking experiments carried out on VEGFR-2 and p38 MAPK crystallographic structures revealed that the active compounds bind to the active sites through H-bonds, arene-cation, and hydrophobic π-π interactions. QSAR analysis demonstrated considerable correlation coefficient (R = 0.76969) and root mean square error (RMSE = 0.10446) values. Also, the residual values between the experimental pIC and predicted pIC are very close, indicating the reliability of the established QSAR model.

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“…Last decade has witnessed that highly toxic low boiling solvents (hexane, DCM, DMF, Chloroform, diethyl ether) were easily replaced by non toxic and high boiling ones (H 2 O, PEGs, ScCO 2 , Glycerol and Ionic Liquids) . Use of these green solvents demonstrated some outstanding findings in terms of better solvating ability, high durability, excellent stability, recyclability, reuse and eco‐compatibility . Practically it has been proved that these new and innovative solvents sometimes perform dual role of catalyst and solvent in the same reaction profile .…”

Section: Introductionmentioning

confidence: 99%

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

et al. 2017

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Efficient and environmentally benign heterocyclization via Knoevenagel condensation followed by [4 + 2] cycloaddition resulting the synthesis of tetrahydro-1H-pyrano[2,3-d]pyrimidine derivatives starting from 2-thiobarbutiric acid, aldehydes and alkyne has been reported. Easily available ethylene glycol was used as a green promoting medium as well as solvent for the reaction progress. This methodology offers a metal and base free approach which endowed high yields with mild reaction conditions and better functional group tolerating ability. Further visible light as a source of energy, recyclability and reuse of ethylene glycol add the methodology a wide scope.

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Visible light promoted synthesis of dihydropyrano[2,3-c]chromenes via a multicomponent-tandem strategy under solvent and catalyst free conditions

Abstract: First photoactivated, highly efficient, one pot, ‘real’ green synthesis of highly functionalized dihydropyrano[3,2-c]chromenes is reported.

Cited by 60 publications

References 71 publications

Visible Light‐Induced Synthesis of Biscoumarin Analogs under Catalyst‐Free Conditions

Visible Light‐Induced Synthesis of Biscoumarin Analogs under Catalyst‐Free Conditions

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

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