scholarly journals Trifluoroacetic Acid as an Effective Catalyst for Biginelli Reaction: One-Pot, Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (and-Thiones)

2011 ◽  
Vol 8 (s1) ◽  
pp. S266-S270 ◽  
Author(s):  
Mohammad R. Mohammadizadeh ◽  
Neda Firoozi
Keyword(s):  
Trifluoroacetic Acid ◽  
Biginelli Reaction ◽  
One Pot ◽  
Dicarbonyl Compounds ◽  
Effective Catalyst

Trifluoroacetic acid (TFA) is introduced as an effective catalyst for promotion of Biginelli reaction. 3,4-Dihydropyrimidin-2(1H)-one (-thione) derivatives (DHPMs) were simply and efficiently prepared using TFA catalyzed one-pot, three-component condensationβ-dicarbonyl compounds, aldehydes and urea (thio).

scholarly journals One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4152
Author(s):  
Jessica Bais ◽  
Fabio Benedetti ◽  
Federico Berti ◽  
Iole Cerminara ◽  
Sara Drioli ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Biginelli Reaction ◽  
Guanidine Hydrochloride ◽  
One Pot ◽  
Dicarbonyl Compounds ◽  
One Pot Synthesis ◽  
Bace 1

A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

Ascorbic acid-Catalyzed One-Pot Three-Component Biginelli Reaction: A Practical and Green Approach towards Synthesis of 3,4-dihydropyrimidin- 2(1H)-ones/thiones

2013 ◽  
Vol 10 (7) ◽  
pp. 463-467 ◽  
Author(s):  
Imene Sehout ◽  
Raouf Boulcina ◽  
Boudjemaa Boumoud ◽  
Fabienne Berree ◽  
Bertrand Carboni ◽  
...  
Keyword(s):  
Ascorbic Acid ◽  
Biginelli Reaction ◽  
One Pot ◽  
Green Approach ◽  
Acid Catalyzed

Vegetable oil as a highly effective 100% bio-based alternative solvent for the one-pot multicomponent Biginelli reaction

2021 ◽  
Author(s):  
Pakin Noppawan ◽  
Suwiwat Sangon ◽  
Nontipa Supanchaiyamat ◽  
Andrew J. Hunt
Keyword(s):  
Vegetable Oil ◽  
Palm Oil ◽  
Biginelli Reaction ◽  
Environmentally Friendly ◽  
One Pot ◽  
Highly Effective ◽  
The One ◽  
Biginelli Reactions

Multicomponent one-pot Biginelli reactions have been successfully performed using vegetable oil as bio-based, non-toxic, and environmentally friendly solvents. Palm oil was demonstrated to be a highly effective greener solvent as...

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