| Dihydropyrimidinones and their derivatives?DHPMs?exhibit extensive and important biological and pharmacological activities,such as antiviral,antibacterial,anticancer,and antihypertensive.The classical synthesis method of DHPMs was the Biginelli reaction,which involves one-pot three-components of aromatic aldehyde,ethyl acetoacetate and urea catalyzed by HCl.With the continuous study on DHPMs,a large number of researches have been carried out on the selection of catalysts,the optimization of reaction conditions,and the extension of the range of raw materials.Therefore,the yield,reaction time,and the diversity of product structure has been improved and developed.Meantime,many novel multifunctional dihydropyrimidinones derivatives have been obtained.Inthisthesis,theresearchprogressofthesynthesisof3,4-dihydropyrimidinones derivatives was reviewed.The synthesis method of N1-substituted3,4-dihydropyrimidinonesderivativeswasimproved.The microscopic morphology and fluorescence properties of them were explored preliminarily.The research results are as follows:1.ThirtyN1-substituted3,4-dihydropyrimidinonesderivativeswere synthesized by an one-pot three-component reaction of aromatic aldehyde,methyl acetoacetate?ethyl ester?and mono-substituted?thio?urea(n?aromatic aldehyde?:n?acetoacetate?:n?mono-substituted?thio?urea?=1:1:1.3)catalyzed by 5 mol%cerous p-toluenesulfonate at 80? under solvent-free conditions,and eighteen of them are new products.The reaction shows the advantages of simple operation,non-toxicity,simple post-treatment,multiple structures of the obtained target compounds,high catalytic activity and wide application range.2.Fourteen N1-methyl substituted 3,4-dihydropyrimidinones derivatives were synthesized by an one-pot three-component reaction of aromatic aldehyde,ethyl benzoylacetate and methylurea or methylthiourea(n?aromatic aldehyde?:n?ethyl?ethyl benzoylacetate:n?methylurea or methylthiourea?=1:1:1)catalyzed by 3 mol%cerous p-toluenesulfonate at 80? under solvent-free conditions,and ten of them are new products.The reaction is economical,environment-friendly,and the catalyst has high catalytic activity and could be used repeatedly.3.ThirteenN1-substituted3,4-dihydropyrimidinonesderivativeswere synthesized by an one-pot three-component reaction of aromatic aldehyde,acetoacetanilide and mono-substituted urea(n?aromatic aldehyde?:n?acetoacetanilide?:n?mono-substituted urea?=1:1:1)at 70? under solvent-free conditions without catalyst,and twelve of them are new products.The reaction can obtain the target compound in high yield without catalyst.The reaction condition is mild and environment-friendly.All target compounds were characterized by IR,1H NMR 13C NMR and elemental analysis.Some compounds were analyzed by scanning electron microscopy and solid-state fluorescence spectra.The results showed that the target compounds are diverse in morphology and have good fluorescent properties.In addition,the structures of three target compounds were confirmed by single crystal X-ray crystallographic analysis. |
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