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

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Author(s): Zainab Ehsani-Nasab, Ali Ezabadi*.

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

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Abstract:

Aim and 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 are characterized by IR, 1H NMR, 13C NMR, and also by their melting points.

Results: In this research, a library of dihydropyrimidinone derivatives were synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as the 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.

Keywords: dicationic ionic liquid, solvent-free conditions, catalyst, 3, 4-dihydropyrimidin-2(1H)-ones, three-component condensation, Brönsted acidic ionic liquid

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Article Details

(E-pub Ahead of Print)
DOI: 10.2174/1386207323666200127113743
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