Synthesis of 3 , 4 -Dihydropyrimidin -2(1H)-Ones Using Protic Acid Surfactant and Sy nergistic Catalysis

Journal of Liaoning Petrochemical University ›› 2006, Vol. 26 ›› Issue (1): 16-18.

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Synthesis of 3 , 4 -Dihydropyrimidin -2(1H)-Ones Using Protic Acid Surfactant and Sy nergistic Catalysis

School of Petrochemical Technology , Liaoning University of Petroleum & Chemical Technology ,
Fushun Liaoning 113001, P .R .China

Received:2005-09-05 Published:2006-01-25 Online:2006-01-25

表面活性剂和质子酸协同催化合成3 , 4 -二氢嘧啶-2 -酮

周海霞, 何　淼, 刘春生, 罗根祥^＊

辽宁石油化工大学石油化工学院, 辽宁抚顺113001

作者简介:周海霞(1977 -), 女, 甘肃靖远县, 在读硕士。

Abstract

Abstract:

　 The yield of the classical Biginelli reaction is low(20 %～ 50 %)when hydrochloric acid is used as catalyst , but synergistic catalysis of surfactant combined with proton acid could accelerate the Biginelli reaction effectively .3, 4-Dihydropy rimidin-2(1H)-ones was synthesized under the condition of β -cyclodextrin as surfactant combined with hydrochloric acid in ethanol solution, and the condensation substrates were benzaldehyde , β -ketoacid ester and urea .The effects of substrate mole ratio , reaction time , the amount of β - cyclodextrin and other surfactants on the yields were investigated.The results show that the yield of 3 , 4 - dihydropyrimidin -2(1H)-ones is up to 92 %, under the conditions of 1.0∶1 .2∶1 .5 mole ratio of benzaldehyde , β -ketoacid ester and urea , 2.5mmol β -cyclodextrin, 0.25mL hydrochloric acid, 25mL ethanol, and 8 hours refluxing time .

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Key words: Surfactant , 　Synthesis, 　3, 4-Dihydropy rimidin-2(1H)-ones

摘要： 　经典的Biginelli 反应用盐酸作催化剂, 通常收率较低(20 %～ 50 %), 而表面活性剂和质子酸协同催化能有效的促进Biginelli 反应进行。以苯甲醛、β -酮酸酯和尿素三组分为反应物, 再加入表面活性剂(β -环糊精)和盐酸, 用乙醇作溶剂, 缩合制备3 , 4-二氢嘧啶-2 -酮。考察了反应物摩尔比、反应时间、β -环糊精的物质的量和不同表面活性剂等因素对收率的影响。结果表明, 在苯甲醛、β -酮酸酯、尿素的摩尔比为1.0∶1.2∶1.5, β -环糊精的物质的量为2.5 mmol, 浓盐酸的体积为0 .25 mL , 乙醇的体积为25 mL , 回流时间为8 h 的条件下, 3 , 4-二氢嘧啶-2-酮收率达到92%。

关键词: 　表面活性剂, 　合成, 　3, 4 -二氢嘧啶-2-酮

CLC Number:

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ZHOU Hai -xia,HE Miao,et al. Synthesis of 3 , 4 -Dihydropyrimidin -2(1H)-Ones Using Protic Acid Surfactant and Sy nergistic Catalysis[J]. Journal of Liaoning Petrochemical University, 2006, 26(1): 16-18.

周海霞, 何　淼, 刘春生, 罗根祥. 表面活性剂和质子酸协同催化合成3 , 4 -二氢嘧啶-2 -酮[J]. 辽宁石油化工大学学报, 2006, 26(1): 16-18.

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Synthesis of 3 , 4 -Dihydropyrimidin -2(1H)-Ones Using Protic Acid Surfactant and Sy nergistic Catalysis

表面活性剂和质子酸协同催化合成3 , 4 -二氢嘧啶-2 -酮

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