Synthesis of 3,4-dihydropyrimidin-2(1H)-one-phosphonates by the microwave-assisted Biginelli reaction

Popovics-Tóth, Nóra and Tajti, Ádám and Hümpfner, Evelyn and Bálint, Erika (2021) Synthesis of 3,4-dihydropyrimidin-2(1H)-one-phosphonates by the microwave-assisted Biginelli reaction. CATALYSTS, 11 (1). pp. 1-15. ISSN 2073-4344

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Abstract

The synthesis of novel 3,4-dihydropyrimidin-2(1H)-one-phosphonates was elaborated by the microwave (MW)-assisted three-component Biginelli reaction of β-ketophosphonates, aromatic or aliphatic aldehydes and urea derivatives. The condensation was optimized on a selected model reaction in respect of the reaction parameters, such as the heating method, the type of the catalyst and solvent, the temperature, the reaction time and the molar ratio of the starting materials. The fast and solvent-free MW-assisted procedure was then extended for the preparation of further new 3,4-dihydropyrimidin-2(1H)-one-phosphonate derivatives starting from different aromatic aldehydes, β-ketophosphonates and urea derivatives to prove the wide scope of the process. As a novel by-product of the Biginelli-type synthesis of 3,4-dihydropyrimidin-2(1H)-one-phosphonates, the 5-diethoxyphosphoryl-4-phenyl-6-styryl-3,4-dihydropyrimidin-2(1H)-one was also isolated and characterized. Our MW-assisted method made also possible the condensation of aliphatic aldehydes, diethyl (2-oxopropyl) phosphonate and urea, which reaction was previously reported to be impossible in the literature.

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