Cerium (IV) sulfate: A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions

Davoodnia, Abolghasem; Khashi, Maryam; Tavakoli‐Hoseini, Niloofar

doi:10.1016/s1872-2067(14)60041-3

Cited by 13 publications

(5 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a consequence of our interest in developing new efficient synthetic methodologies [43][44][45][46][47] for the synthesis of bioactive molecules and owing to the biological significance of 1,2,4,5-tetrasubstituted imidazoles, we wish to report herein a solvent-free synthesis of 1,2,4,5-tetrasubstituted imidazoles catalyzed by Fe 3 O 4 @SiO 2 -OSO 3 H, as a green and effective magnetically recyclable heterogeneous catalyst (Scheme 1).…”

Section: Oriental Journal Of Chemistrymentioning

confidence: 99%

Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nano Fe3O4@SiO2-OSO3H as a Stable and Magnetically Recyclable Heterogeneous Catalyst

Yadegarian¹,

Davoodnia²,

Nakhaei³

2015

Orient. J. Chem

Self Cite

View full text Add to dashboard Cite

Nano-Fe 3 O 4 encapsulated-silica particles bearing sulfonic acid groups (Fe 3 O 4 @SiO 2 -OSO 3 H) has been used as an efficient and magnetically separable heterogeneous catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by one-pot, four-component reaction of benzil, aromatic aldehydes, primary amines, and ammonium acetate under neat conditions. The effect of various reaction parameters, such as reaction temperature, catalyst loading and solvent effect, were studied. The desired products are obtained in relatively short reaction times with high yields. Importantly, the catalyst could be easily separated from the reaction mixture by a permanent magnet and reused for several times without the significant loss of its activity.

show abstract

Section: Oriental Journal Of Chemistrymentioning

confidence: 99%

Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nano Fe3O4@SiO2-OSO3H as a Stable and Magnetically Recyclable Heterogeneous Catalyst

Yadegarian¹,

Davoodnia²,

Nakhaei³

2015

Orient. J. Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…Considering the importance of these compounds, several methods have been revealed for the synthesis of 2,3-dihydroquinazolin-4(1 H )-ones. They are usually synthesized by three-component reactions of aldehydes, isatoic anhydrides, primary amines, or ammonium salts, in the presence of numerous catalysts, under different circumstances. − Some of these reagents or catalysts are cerium(IV) sulfate, (Cu-CNTs), choline chloride in the presence of malonic acid, silica-bonded propyl- S -sulfonic acid (SBSSA), silica-bonded N -propyl sulfamic acid (SBNPSA), and Al(H 2 PO 4 ) 3 . Some of these methods have limitations such as long reaction time, high-temperature reaction, side reactions producing a mixture of products and complex separation, and purification methods.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines

2019

View full text Add to dashboard Cite

A series of new quinazoline derivatives were designed and synthesized via a one-pot condensation reaction between isatoic anhydride and aromatic aldehydes with anilines using aluminum sulfate as a catalyst in refluxing ethanol. Their structures were confirmed by their physical, IR, 1H NMR, 13C NMR, and mass spectroscopy data and evaluated for some biological effects, including the antioxidant and α-glucosidase inhibitory activities as well as some in vivo hematological parameters. The ability of synthesized compounds in the inhibition of α-glucosidase was also investigated through the in silico study. The significant and important changes in some hematological tests were perceived. Notably, compound 4h showed more reducing effects on cholesterol and triglyceride levels. This molecule certainly has the potential to be developed as the antihyperlipemic compound. The tested compounds, in particular, compounds 4j and 4l, were found to be uniquely reducing blood sugar levels. The entire synthesized compounds showed the potent α-glucosidase inhibitory activity compared with acarbose as a standard material. Amongst, the compounds 4h and 4i showed the strongest enzyme inhibitory potentials than the standard drug acarbose. There was a good correlation between in vitro and in silico studies for ligands 4i and 4l. The majority of compounds presented a good radical scavenging activity, though the compound 4j exhibited the strongest activity, even to the standard of ascorbic acid. Further studies are required to determine whether these main compounds could be a potential treatment for diabetes and hyperlipidemia diseases.

show abstract

“…Some Lewis acid catalysts had the advantage of being easily recovered after the reaction and recycled several times without considerable loss of reactivity. 63,64,66,71 …”

Section: Introductionmentioning

confidence: 99%

2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design

2018

View full text Add to dashboard Cite

show abstract

Cerium (IV) sulfate: A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions

Cited by 13 publications

References 39 publications

Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nano Fe3O4@SiO2-OSO3H as a Stable and Magnetically Recyclable Heterogeneous Catalyst

Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nano Fe3O4@SiO2-OSO3H as a Stable and Magnetically Recyclable Heterogeneous Catalyst

Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines

2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design

Contact Info

Product

Resources

About