有机化学 ›› 2014, Vol. 34 ›› Issue (8): 1669-1672.DOI: 10.6023/cjoc201402018 上一篇    下一篇

研究简报

C(5)-对甲基苯甲酰取代的3,4-二氢嘧啶(硫)酮类化合物的微波无溶剂合成

李丽, 刘庆俭, 隋雪燕   

  1. 山东师范大学化学化工与材料科学学院 济南 250014
  • 收稿日期:2014-02-17 修回日期:2014-03-13 出版日期:2014-08-25 发布日期:2014-04-28
  • 通讯作者: 刘庆俭 E-mail:liuqj@sdnu.edu.cn

Synthesis of C(5)-(p-Toluoyl substituted)-3,4-dihydropyrimi- dinones (or -thiones) via Biginelli Reaction Promoted with Microwave Irradiation under Solvent-Free Conditions

Li Li, Liu Qingjian, Sui Xueyan   

  1. College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014
  • Received:2014-02-17 Revised:2014-03-13 Online:2014-08-25 Published:2014-04-28

Biginelli反应是约120年前意大利化学家Pietro Biginelli发现的,所涉及的就是乙酰乙酸乙酯、尿素和芳基醛的一锅酸催化环化缩合反应. 大量的研究表明Biginelli反应的产物——二氢嘧啶酮类化合物因为具有显著的生理和药理活性以及结构变化的多样性使得人们对于Biginelli反应的关注度持续增高. 讲述了在微波无溶剂条件下,通过醛、对甲基苯甲酰丙酮、尿素(硫脲)在对甲苯磺酸催化下进行的Biginelli反应的方法来合成5-(4-甲基苯甲酰基)-3,4-二氢嘧 啶-2(1H)-酮(硫酮)类衍生物,不仅易得到且收率高.

关键词: Biginelli反应, 3,4-二氢嘧啶-2(1H)-酮(或-硫酮), β-二酮, 微波辐射

The Biginelli reaction, which involves the one-pot acid catalyzed cyclocondensation of ethyl acetoacetate, urea, and arylaldehyde, was first discovered by Italian chemist Pietro Biginelli about 120 years ago. A large number researchers have shown persistent attention to the study of Biginelli reaction on account of its significant biological and pharmaceutical activities and diversity of structural changes of dihydropyrimidines (DHPMs) and its derivatives. Herein, the synthesis of C(5)-(p-toluoyl)-3,4-dihydropyrimidin-2(1H)-ones (or -thiones) via Biginelli reaction has been accomplished from aldehydes, p-toluoylacetone, and urea or thiourea in the presence of TsOH promoted with microwave irradiation under solvent-free conditions in good yields and high purity without chromatographic separation.

Key words: Biginelli reaction, 3,4-dihydropyrimidin-2(1H)-ones (or -thiones), β-diketone, microwave irradittion