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An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Thiones Catalyzed by a Novel Brønsted Acidic Ionic Liquid Under Solvent-free Conditions

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2015 Mar 3
PMID 25730389
Citations 12
Authors
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Abstract

We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Brønsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli reaction conditions, the present method has the advantages of giving good yields, short reaction times, near room temperature conditions and the avoidance of the use of organic solvents and metal catalyst.

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References
1.
Ma Y, Qian C, Wang L, Yang M . Lanthanide triflate catalyzed Biginelli reaction. one-pot synthesis of dihydropyrimidinones under solvent-free conditions. J Org Chem. 2000; 65(12):3864-8. DOI: 10.1021/jo9919052. View

2.
Kappe C . Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc Chem Res. 2000; 33(12):879-88. DOI: 10.1021/ar000048h. View

3.
Kappe C . Biologically active dihydropyrimidones of the Biginelli-type--a literature survey. Eur J Med Chem. 2001; 35(12):1043-52. DOI: 10.1016/s0223-5234(00)01189-2. View

4.
Welton T . Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis. Chem Rev. 2002; 99(8):2071-2084. DOI: 10.1021/cr980032t. View

5.
Li J, Han J, Yang J, Li T . An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation. Ultrason Sonochem. 2003; 10(3):119-22. DOI: 10.1016/S1350-4177(03)00092-0. View