无溶剂条件下三氯化铁高效催化合成N1-取代的3,4-二氢嘧啶-2(1H)-酮  

Efficient synthesis of N1-substituted 3,4-dihydropyrimidone-2(1H)-onescatalyzed by ferric(Ⅲ)chloride under solvent-free conditions

作　　者：王敏[1] 张顺[1] 姜宏旭[1] WANG Min;ZHANG Shun;JIANG Hong-xu(College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121013, China)

机构地区：[1]渤海大学化学化工学院,辽宁锦州121013

出　　处：《渤海大学学报（自然科学版）》2017年第4期289-294,共6页Journal of Bohai University:Natural Science Edition

基　　金：国家自然科学基金项目(No:21406016);辽宁省高等学校优秀人才支持计划(No:LJQ2015002);辽宁省自然科学基金项目(No:2015020201)

摘　　要：无溶剂、80℃条件下,三氯化铁为催化剂,芳香醛、β-酮酯、单取代(硫)脲三组分"一锅法"高效合成了一系列N1-取代的3,4-二氢嘧啶酮.考察了原料配比、催化剂用量和反应温度对产率的影响,确定较佳反应条件为:n_醛:n_酯:n_脲=1:1:1,三氯化铁3 mol%,反应温度80℃.在较佳反应条件下,考察了各种芳香醛、乙酰乙酸乙酯(乙酰乙酸甲酯)、单取代脲(硫脲)的反应效果,并合成了八种新物质.所有产品结构通过IR、1H NMR、13C NMR和元素分析进行表征.最后提出了可能的催化作用机理.该方法具有操作简单、不使用任何有机溶剂、反应条件温和、催化剂廉价易得、底物范围广等优点.A series of N1-substituted3,4-dihydropyrimidone-2(1H)-ones were synthesized by an one-pot three-component condensation of aromatic aldehydes,β-ketone esters and monosubstituted(thio)urea in the presence of FeCl3·6H2O under solvent-free conditions at80℃.The effects of the ratio of the raw materials,the amount of the catalyst and thereaction temperature on the yields were investigated.The optimal conditions are as follows:naldehyde:nester:nurea=1:1:1,FeCl3·6H2O is3mol%,reaction temperature is80℃.The reactions of various aromatic aldehydes,ethyl acetoacetate(methyl acetoacetate)and monosubstituted(thio)urea were investigated.Eight new compounds were synthesized.All products were characterized by IR,1H NMR,13C NMR and elemental analysis.The probable catalytic mechanism was proposed.The method has the advantages of simple procedure,the avoidance of the use of organic solvents,mild conditions,inexpensive catalyst and extensive substrates.

关 键 词：3 4-二氢嘧啶酮 三氯化铁 无溶剂 BIGINELLI反应 

分 类 号：O626.4[理学—有机化学]