4-苯基-5-乙氧羰基-6-甲基-3,4-二氢嘧啶-2(1H)-酮的绿色合成研究
Environmentally synthesis of 4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropirimidine-2(1H)-one
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摘要: 目的 探索操作简便,环境友好的4-苯基-5-乙氧羰基-6-甲基-3,4-二氢嘧啶-2(1H)-酮的合成方法。 方法 以苯甲醛、乙酰乙酸乙酯和尿素作为起始原料,在无溶剂和微波加热条件下,选择1-丁基-3-甲基咪唑氯盐和1-丁基-3-甲基咪唑-L-乳酸盐两种不同的离子液体分别催化Biginelli反应制备4-苯基-5-乙氧羰基-6-甲基-3,4-二氢嘧啶-2(1H)-酮,并比较两种离子液体的催化效果。 结果 两种离子液体在微波、无溶剂条件下均可催化Biginelli反应制得目标化合物,其中1-丁基-3-甲基咪唑-L-乳酸盐作为催化剂目标化合物收率较高。 结论 以离子液体-丁基-3-甲基咪唑-L-乳酸盐作为催化剂,经微波、无溶剂Biginelli反应制备4-苯基-5-乙氧羰基-6-甲基-3,4-二氢嘧啶-2(1H)-酮,是一种易于操作的绿色合成方法。Abstract: Objective To explore an easily-controled, environmentally benign synthetic method of 4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropirimidine-2(1H)-one. Methods 4-phenyl-5-ethoxy-carbonyl-6-methyl-3,4-dihydropirimidine-2(1H)-one was synthesized from benzaldehyde, ethyl acetoacetate and urea through the Biginelli reaction catalysed by two different ionic liquid (1-butyl-3-methylimidazolium chloride and 1-butyl-3-methylimidazolium (L)-lactate) under microwave irradiation without a solvent respectively. Results Both ionic liquid catalysts could catalyse Biginelli reaction to get the title compound under microwave irradiation without a solvent. Compared with 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium (L)-lactate was a better catalyst to get a more satisfied yield of the title compound. Conclusion Microwave accelerated solvent-free Biginelli reaction using green ionic liquid of 1-butyl-3-methylimidazolium (L)-lactate as catalyst was a convenient and environmentally benign synthetic method of 4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropirimidine-2(1H)-one.
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[1] Dennis R , Edilson VB, Gabriela SR, et al. Multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones with a Cu/silica xerogel composite catalyst[J]. Letters in Organic Chemistry , 2007 , 4 ( 1 ) :39. [2] Christophe L, Jean J, Vanden E, et al. Ionic liquid phase organic synthesis (IoLiPOS) methodology applied to the preparation of new 3,4-dihydropyrimidine-2(1H)-ones bearing bioisostere group in N-3 position[J]. Tetrahedron , 2008 , 64 ( 22 ) :5328. [3] 彭家建,邓友全. 室温离子液体催化 "一锅法"合成3,4 -二氢嘧啶-2-酮[J]. 有机化学 , 2002 , 1 ( 22 ) : 71. [4] 邵国强. 离子液体中微波促进的Biginelli缩合反应[J]. 合成化学 , 2004 , 12 ( 4 ) :325. [5] Toma NG, Heather T, Oliver K, et al. Integration of high speed microwave chemistry and a statistical 'design of experiment' approach for the synthesis of the mitotic kinesin Eg5 inhibitor monastrol[J]. Tetrahedron , 2008 , 64 ( 9 ) :2035. [6] Swatlosk RP, Holbrey JD, Rogers RD, et al. Ionic liquids are not always green: hydrolysis of l-butyl-3-methylimidazolium hexafluorophosphate[J]. Green Chem , 2003 , 5:361. [7] 李 明, 郭维斯, 文丽荣, 等. 新型无毒离子液体催化"一锅煮"合成3,4-二氢嘧啶2-(1H)-酮[J]. 有机化学 , 2005 , 25 ( 9 ) :1062. [8] 王伟超, 吴林波, 李伯耿, 等. 1-烷基-3-甲基咪唑-L-乳酸盐的合成及其物理性质[J]. 应用化学 , 2007 , 24 ( 4 ) :378. [9] 李长多, 张学俊. 1,3-二烷基咪唑类离子液体的合成研究[J]. 化工中间体 , 2008 , 11:63. [10] Abdelmadjid D, Mouna A, Ali B, et al. A one-pot Biginelli synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base[J]. Tetrahedron Letters , 2008 , 49 ( 42 ) :6119. -
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