Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4<i>H</i>-pyrans

Guo, Ruiyun; An, Zhi-Min; Mo, Li‐Ping; Wang, Ruizhi; Liu, Hongxia; Wang, Shuxia; Zhang, Zhan‐Hui

doi:10.1021/co400107j

Cited by 159 publications

(45 citation statements)

References 47 publications

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“…Environmentally benign selective catalytic reactions are urgently needed in the pharmaceutical and chemical industries; therefore, our fundamental objective is to produce a greener technology that is simple, cleansed, and more effective than conventional reaction . Centering our research interests on the development of efficient ecofriendly methodology, the versatility of meglumine as catalyst was extended for the synthesis of 5‐hydroxy‐2‐(hydroxymethyl)‐4 H ‐pyran‐4‐one derivatives successfully via a new, fast, and profitable process in good yields . Our newly synthesized compounds were evaluated for their antioxidant activities, and docking studies provided valuable information that 3MNG protein exhibits effective binding interaction against the active compound.…”

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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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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“…), Meglumine (2013, Zhang et al . ), N ,2‐Dibromo‐6‐chloro‐3,4‐dihydro‐2 H ‐benzo[ e ][1,2,4]thiadiazine‐7‐sulfonamide 1,1‐dioxide (DCDBTSD) (2015, Khazaei et al . ), Copper (II) acetate monohydrate (2016, Maghsoodlou et al .…”

Section: Introductionmentioning

confidence: 99%

Urea‐Catalysed Access to Novel Spirooxindole Benzopyrans via Domino Multicomponent Cascade: Approach Towards Sustainability

Bagchi¹,

Hussen²,

Deeksha³

et al. 2019

ChemistrySelect

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A multicomponent one-pot domino reaction of 1-hydroxy-3Hbenzo[f]chromen-3-one, isatin and malononitrile/ethyl cyanoacetate is herein investigated. The methodology concludes to synthesize diversified novel spiro-benzo[f]pyranochromene derivatives in good to excellent yields. This method is compatible with different unsubstituted and substituted isatins bearing electron-donating and electron-withdrawing groups. The operational simplicity, short reaction time along with the gram scale up protocol make this synthetic process suitable for both academia as well as industry.

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“…Furthermore, they can be used in several neurodegenerative diseases, such as parkinson, alzheimer, down syndrome, huntington, schizophrenia and myoclonus diseases as cognitive enhancer . Numerous method have been reported for the synthesis of these compounds via three‐component reaction of aldehyde, malononitrile and various β ‐diketones using various conditions like microwave and ultrasonic irradiation . A variety of reagents such as Yb(PFO) 3 , LiBr, SB‐DABCO, tetrabutylammonium bromide (TBAB), Na 2 SeO 4 , solid acids, diammonium hydrogen phosphate, silica bonded n‐propyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride and DBU were employed for the preparation of pyrans.…”

Section: Introductionmentioning

confidence: 99%

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Hojati

Amiri

MoeiniEghbali

et al. 2018

Applied Organom Chemis

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Polypyrrole (PPY)/Fe 3 O 4 /CNT has been synthesized and characterized by FT-IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4Hpyran-3-carboxylates, 4H,5H-pyrano[3,2-c]chromenes and dihydropyrano[2,3-c] pyrazoles have been successfully prepared from one-pot three-component condensation of aldehyde, malononitrile and active methylene-containing compounds (dimedone /ethyl acetoacetate/4-hydroxycoumarin/3-methyl-2pyrazoline-5-one) using PPY/Fe 3 O 4 /CNT as a new and reusable heterogeneouscatalyst. The present method offer several advantages such as; high yields of products, short reaction times, easy work-up procedure and easy separation of the catalyst from the reaction mixture due to its magnetic character. Furthermore, chemoselective synthesis of bis-benzo[b]pyran from terephthalaldehyde can be achieved by this method.

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Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4H-pyrans

Cited by 159 publications

References 47 publications

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

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

Urea‐Catalysed Access to Novel Spirooxindole Benzopyrans via Domino Multicomponent Cascade: Approach Towards Sustainability

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

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Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4H-pyrans

Cited by 159 publications

References 47 publications

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

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

Urea‐Catalysed Access to Novel Spirooxindole Benzopyrans via Domino Multicomponent Cascade: Approach Towards Sustainability

Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

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Product

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Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives