Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Kakanejadifard, Ali; Azarbani, Farideh; Khosravani, Nasim; Notash, Behrouz

doi:10.1016/j.molliq.2016.05.047

Cited by 11 publications

(5 citation statements)

References 32 publications

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“…[1][2][3] Chromenes demonstrate a diverse range of biological activities, such as anti-anaphylactic activity, antimicrobial, anticancer properties, diuretic, and spasmolytic, and are also used to synthesize tacrine analogs and the blood anticoagulant warfarin. 4,5 Chromene derivatives also form components of many natural products such as calanolides, calophyllolide, and calanone. 6 In addition, pyrano [3,2-c]chromenes exhibit a wide range of biological activities, including against Alzheimer's disease, schizophrenia, and AIDS-associated dementia, making them valuable synthons for the synthesis of pharmacological agents.…”

Section: Introductionmentioning

confidence: 99%

A novel magnetic FSM-16 supported ionic liquid/Pd complex as a high performance and recyclable catalyst for the synthesis of pyrano[3,2-c]chromenes

Jahanbakhshi,

Farahi

2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

A novel magnetic FSM-16 supported ionic liquid/Pd complex as a high performance and recyclable catalyst for the synthesis of pyrano[3,2-c]chromenes

Jahanbakhshi,

Farahi

2024

RSC Adv.

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“…[15,16] Chromene derivatives have displayed a wide range of biological activities such as antibacterial, antifungal, anti-influenza, antimalarial, anticoagulant, antitumor, anticancer, and anti-HIV. [17][18][19] Hence, design and synthesis of pharmacophores in medicinal chemistry and drug development could be performed by modeling chromene-like structure found in plant. [20] Also, chromenes included 3-substituted coumarin, 3-substituted indole, β-naphthol, and indandion derivatives are found in some natural and medicinal compounds, while there are very few papers for their synthesis.…”

Section: Introductionmentioning

confidence: 99%

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Ghavidel

Mirza

Soleimani‐Amiri

et al. 2020

J Chinese Chemical Soc

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A green synthesis of functionalized 4H-chromenes using one-pot, threecomponent reaction of salicylaldehyde (1), active methylene (2), and carbonbased nucleophile (3) using Fe 3 O 4 @CONa nanoparticles in water has been performed at 60 C. The Fe 3 O 4 @CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst and solvent, short reaction time, high product yields, as well as simple work-up procedure were found as some advantages of this methodology. The density functional theory calculations were applied to all-inclusive perception of the one-pot, three-component reaction mechanism. The most reactions progressed through the following route: (a) nucleophilic addition of 2 to 1; (b) ring closing, dehydration; (c) nucleophilic substitution of 3 (2-naphtol, 4-hydroxycumarin) to intermediate. Sometimes mechanism mutated to: (a) nucleophilic addition of 3 (indole, 2-methylindole) to 1, and dehydration; (b) nucleophilic addition of 2 to intermediate; and (c) ring closing, and dehydration. The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms. Theoretical study could be so helpful to pick out suitable reactants of the reaction.

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“…Therefore, for synthetic organic chemists, these compounds are capable of functioning as both starting and intermediate material in many chemical reactions. For instance, 2‐(4‐nitrobenzylidene)malononitrile and 2‐(3,4,5‐trimethoxybenzylidene)malononitrile are well known as potent tyrosine kinase inhibitors, and 2‐amino‐7‐hydroxy‐4‐phenyl‐4H‐chromene‐3‐carbonitrile exhibits activity against the gram‐positive bacteria Bacillus cereus, Staphylococcus aureus and Staphylococcus epidermidis …”

Section: Introductionmentioning

confidence: 99%

Pd nanoparticles Incarcerated in Aluminium Oxy‐Hydroxide: An Efficient and Recyclable Heterogeneous Catalyst for Selective Knoevenagel Condensation

Göksu

Gültekin

2017

ChemistrySelect

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Knoevenagel condensation between aryl aldehyde derivatives with malononitrile was successfully achieved using commercially available Pd/AlO(OH) nanoparticles (0.5 wt% Pd) in an aqueous medium. All benzylidenemalononitrile (BMN) derivatives were obtained promptly (8‐60 min) with high selectivity and yields of over 99 % in a mixture of H2O/MeOH (v/v=1/2) at room temperature. Moreover, when benzoyl chloride derivatives were utilized instead of aryl aldehyde derivatives, medium amounts of the expected products were yielded. Before the reaction and after five reuses, characterization of the Pd/AlO(OH) nanoparticles was carried out via X‐ray diffraction and scanning electron microscopy analysis. The BMN derivative characterization was accomplished using the 1H NMR and 13C NMR spectra. In order to optimize the reaction conditions, the parametric effects of the solvent type and catalyst amount were examined. Consequently, the PdAlO(OH) NPs were used for the first time in the Knoevenagel condensation. A novel, practical and eco‐friendly process was developed for Knoevenagel condensation in the presence of Pd/AlO(OH) nanoparticles.

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Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Cited by 11 publications

References 32 publications

A novel magnetic FSM-16 supported ionic liquid/Pd complex as a high performance and recyclable catalyst for the synthesis of pyrano[3,2-c]chromenes

A novel magnetic FSM-16 supported ionic liquid/Pd complex as a high performance and recyclable catalyst for the synthesis of pyrano[3,2-c]chromenes

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Pd nanoparticles Incarcerated in Aluminium Oxy‐Hydroxide: An Efficient and Recyclable Heterogeneous Catalyst for Selective Knoevenagel Condensation

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