期刊
CATALYSTS
卷 11, 期 1, 页码 -出版社
MDPI
DOI: 10.3390/catal11010045
关键词
heterocyclic phosphonates; 3; 4-dihydropyrimidin-2(1H)-one-phosphonates; multicomponent reactions; Biginelli reaction; microwave
资金
- Hungarian Research Development and Innovation Office [FK123961]
- Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences [BO/00278/17/7, UNKP-20-5-BME-288]
- New National Excellence Program of the Ministry of Human Capacities
The synthesis of novel 3,4-dihydropyrimidin-2(1H)-one-phosphonates was achieved through microwave-assisted Biginelli reaction, optimizing reaction parameters and demonstrating a wide scope of application. By-products of the synthesis were also identified, including a previously reported impossible reaction between aliphatic aldehydes, diethyl (2-oxopropyl)phosphonate, and urea.
The synthesis of novel 3,4-dihydropyrimidin-2(1H)-one-phosphonates was elaborated by the microwave (MW)-assisted three-component Biginelli reaction of beta-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, beta-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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