Alum-catalyzed one-pot synthesis of dihydropyrano[3,2-b]chromenediones

Li, Wei Lin; Wu, Li; Yan, Fu Lin

doi:10.1590/s0103-50532011001100025

Cited by 16 publications

(5 citation statements)

References 11 publications

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“…The synthesis of the dihydropyrano[3,2‐ b ]chromenediones was successfully achieved by employing principles of “green chemistry”, and these included inexpensive off‐the‐shelf catalysts, short reaction times, solvent‐free conditions, straightforward work‐up, and good‐to‐high yielding syntheses …”

Section: Resultsmentioning

confidence: 99%

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Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

et al. 2017

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Inhibition of mushroom tyrosinase was observed with synthetic dihydropyrano[3,2-b]chromenediones. Among them, DHPC04 displayed the most potent tyrosinase inhibitory activity with a K value of 4 μm, comparable to the reference standard inhibitor kojic acid. A kinetic study suggested that these synthetic heterocyclic compounds behave as competitive inhibitors for the L-DOPA binding site of the enzyme. Furthermore, molecular modeling provided important insight into the mechanism of binding interactions with the tyrosinase copper active site.

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Section: Resultsmentioning

confidence: 99%

“…For this study, DHPCs were prepared in racemic form (mixture of enantiomers) via a three‐component condensation reaction of an aromatic aldehyde, dimedone, and KA . To synthesize DHPC03 and DHPC04, chlorokojic acid was used instead (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

et al. 2017

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“…To date, a handful of synthetic approaches have been produced for the synthesis of 5‐hydroxy‐2‐(hydroxymethyl)‐4 H ‐pyran‐4‐one derivatives. In recent years, several reports revealed the usage of InCl 3, FeCl 3 ‐SiO 2, and alums as catalysts in a safe and effective manner in the synthesis of 2‐(hydroxymethyl)‐7, 7‐dimethyl‐10‐aryl‐7, 8‐dihydropyrano[3, 2‐ b ]chromene‐4, 9(6H, 10H)‐diones improved the yields enormously. Due to the fact that, various synthetic transformations have been indulged with some drawbacks in applications of expensive, water‐bigoted and nonrecyclable catalysts.…”

Section: Introductionmentioning

confidence: 99%

A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Sravya

Suresh

Zyryanov

et al. 2019

Journal of Heterocyclic Chem

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A simple method was employed for the synthesis of dihydropyrano [3, 2-b] chromenedione derivatives (4a-o) in high yields by condensation of 5, 5dimethylcyclohexane-1, 3-dione(1), different aromatic aldehydes (2a-o), and 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one(3), using meglumine as a stable and reusable catalyst. Meglumine, an amino sugar, was employed as an environmentally benign catalyst, due to its splendid properties such as being inexpensive, recyclable, and biodegradable. The accomplished protocol employs low catalyst loading and easy work-up for the synthesis of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one derivatives. A great asset is that without any significant loss, the catalyst could be recovered and reused for extended synthetic steps. This offer huge advantage to overcome recyclability issues. Our synthesized compounds were analyzed by IR, 1 H, 13 C NMR, mass spectra and evaluated for their antioxidant properties by 1, 1-diphenyl-2-picryl hydrazyl radical (DPPH), hydrogen peroxide(H 2 O 2 ), and nitric oxide (NO) scavenging methods. The correlation in exhibition of antioxidant activity was effective at all doses. The binding interactions and molecular docking studies for entitled compounds were studied against 3MNG protein; 4k exhibited marked binding affinity with excellent docking score of −7.6 Kcal/mol and emerged as a lead compound.

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“…Three-component reaction of kojic acid, aldehyde and 1,3-dicarbonyl compounds or malononitrile is one of the most important methodology for the synthesis of these heterocyclic systems. A various catalysts and conditions were reported for this reaction, including InCl3, 10 CAN, 11 Al2O3, 12 Bi(OTf)3, 13 CeCl3•7H2O/SiO2, 14 FeCl3-SiO2, 15 Fe3O4@SiO2, 16 ultrasonic irradiation, 17 imidazole, 18 piperidine, 19 Et3N, 20 and NH4VO3. 21 Kojic acid and its derivatives have wide range of applications in cosmetic, 22 medicine, 23 food, 24 agriculture 25 and chemical industries.…”

Section: Introductionmentioning

confidence: 99%

Three-component reactions of kojic acid: Efficient synthesis of Dihydropyrano[3,2-b]chromenediones and aminopyranopyrans catalyzed with Nano-Bi2O3-ZnO and Nano-ZnO

Zirak¹,

Azinfar²,

Khalili³

2017

10.5267/j.ccl

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Synthesis of pyrano-chromenes and pyrano-pyrans was developed by three-component reactions of kojic acid and aromatic aldehydes with dimethone and malononitrile, catalyzed with nano-Bi2O3-ZnO and nano-ZnO, respectively. Reactions proceeded smoothly and the corresponding heterocyclic products were obtained in good to high yields. Nano ZnO and nano Bi2O3-ZnO were prepared by sol-gel method and characterized by X-ray diffraction (XRD), energy-dispersive X-ray analysis (EDX), Fourier transform infrared (FT-IR), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) techniques. Supporting Bi 3+ on ZnO nanoparticles as Bi2O3, is the main novelty of this work. The simple reaction procedure, easy separation of products, low catalyst loading, reusability of the catalyst are some advantageous of this protocol.

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Alum-catalyzed one-pot synthesis of dihydropyrano[3,2-b]chromenediones

Cited by 16 publications

References 11 publications

Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Three-component reactions of kojic acid: Efficient synthesis of Dihydropyrano[3,2-b]chromenediones and aminopyranopyrans catalyzed with Nano-Bi2O3-ZnO and Nano-ZnO

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