标题:The Effects of Different Catalysts, Substituted Aromatic Aldehydes on One-Pot Three-Component Biginelli Reaction
作者:Liu, Zong-liang; Zhang, Ren-mei; Liu, Ye; Guo, Yan; Meng, Qing-guo
作者机构:[Liu, Zong-liang; Zhang, Ren-mei; Liu, Ye; Guo, Yan; Meng, Qing-guo] Yantai Univ, Univ Shandong, Collaborat Innovat Ctr Adv Drug Delivery Syst & B, Mi 更多
通讯作者:Liu, ZL
通讯作者地址:[Liu, ZL]Yantai Univ, Univ Shandong, Collaborat Innovat Ctr Adv Drug Delivery Syst & B, Minist Educ,Sch Pharm,Key Lab Mol Pharmacol & Dru, Yantai 2640 更多
来源:CURRENT ORGANIC SYNTHESIS
出版年:2019
卷:16
期:1
页码:181-186
DOI:10.2174/1570179416666181122100405
关键词:Multicomponent reactions; Biginelli reaction; catalysts; synthetize;; substituents; reaction conditions
摘要:Aim and Objective: The Biginelli reaction, first reported in 1893, is one great example of the important multicomponent reactions reported from 1893. Under the same conditions, the influence of the common catalysts on the yield of the Biginelli reaction was investigated.; Materials and Method: To a round-bottom flask equipped with a spherical condenser were added 1,3-dicarbonyl compound (1.0 eq), urea (1.45 eq), aromatic aldehyde (1.0 eq), catalyst and methanol. The mixture was heated at reflux for 16 h. After cooling off, the mixture was filtered and washed with cold methanol to give DHPMs. Reaction solution was further purified by recrystallization with petroleum ether and ethyl acetate. Six catalytic systems, different 1,3-dicarbonyl compounds and different substituted aromatic aldehydes with varied substitutions are described for the Biginelli reaction. An analysis was also performed to study the factors that affect the yield of the reaction.; Results: When 1,3-dicarbonyl compound was ethyl acetoacetate, the CuCl/ conc.H2SO4 system gave the highest yield (90.5%). While when acetoacetamide was used, the yields of DHPMs in presence of PTSA/conc. HCl, conc. HCl or FeCl3 center dot 6H(2)O were all over 90%. Nine DHPMs with different substituents were obtained.; Conclusion: The Lewis acid or mixed catalyst had no significant advantage over a single protonic acid as catalyst. Conc. HCl as the catalyst was found to be the most effective condition for the preparation of DHPMs. The aromatic aldehyde with weak electron-withdrawing substituent such as Br resulted in the best yield.
收录类别:SCIE
资源类型:期刊论文
TOP