有机化学 ›› 2011, Vol. 31 ›› Issue (06): 855-859. 上一篇    下一篇

研究论文

3-取代-4(3H)-喹唑啉酮在酸性离子液体中的一锅法、微波辅助合成

李心忠*,1,林棋1,吾满江•艾力2   

  1. (1闽江学院化学与化学工程系 福州 350108)
    (2中国科学院新疆理化技术研究所 乌鲁木齐 830011)
  • 收稿日期:2010-10-10 修回日期:2010-12-28 发布日期:2011-02-14
  • 通讯作者: 李心忠 E-mail:lixinzhong77@126.com

One-Pot Synthesis of 3-Substituted-4(3H)-quinazolinones in Acidic Ionic Liquids under Microwave Irradiation Conditions

Li Xinzhong*,1 Lin Qi1 Wumanjiang Eli2   

  1. (1 Department of Chemistry and Chemical Engineering, Minjiang University, Fuzhou 350108)
    (2 Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sci-ences, Urumqi 830011)
  • Received:2010-10-10 Revised:2010-12-28 Published:2011-02-14

研究以二种基于磺酸基官能团的Brønsted 酸性功能化离子液体: 1-(4-磺酸基)苄基-3-甲基咪唑硫酸氢盐(a), N-(4-磺酸基)苄基吡啶硫酸氢根盐(b)作为反应介质与催化剂, 2-氨基苯甲酸、原甲酸酯或甲酸、芳香胺或脂肪胺三组分为原料, 在微波辐射下实现了3-取代-4(3H)-喹唑啉酮的一锅法快速合成. 离子液体加入量10 mol%, 反应时间4~6 min, 目标化合物产率74%~94%. 离子液体可循环使用3次, 催化活性基本保持不变. 此合成方法通用性强, 3-位可引入芳基或烷基取代基, 取代基电性效应小, 拉电子取代基底物也可顺利反应. 另外, 反应可直接以85%甲酸作为C-2引入单元, 目标化合物产率72%~91%.

关键词: Br?nsted酸, 离子液体, 多组分反应, 微波, 4(3H)-喹唑啉酮

Two novel Br?nsted acidic ionic liquids 1-(4-sulfonic)-benzyl-3-methylimidazolium hydrogen sulfate (a) and 1-(4-sulfonic)-benzyl-3-methylpyridium hydrogen sulfate (b) were used as catalyst and medium in the one-pot synthesis of 3-substituted-4(3H)-quinazolinones, using anthranilic acid, triethyl orthoformate or formic acid and aromatic or aliphatic amines as starting materials under microwave irradiation. It was found that the reactions completed within 4~6 min with good to excellent yields (74~94%) in the presence of 10 mol% ionic liquids. The ionic liquids can be recovered easily and recycled three times without any significant loss in catalytic activity. This synthetic method has the advantage of generality. The aromatic or aliphatic substituents can be introduced in the 3-position, the substrates with electron-withdrawing substituents can also take part of the reaction smoothly and offered satisfactory yields. In addition to, this synthetic method can use 85% formic acid directly with yields of 72%~91%.

Key words: Br?nsted acid, ionic liquid, multi-component reaction, microwave, 4(3H)-quinazolinone