有机化学 ›› 2017, Vol. 37 ›› Issue (12): 3191-3197.DOI: 10.6023/cjoc201706015 上一篇    下一篇

研究论文

离子液体中碘催化下2-氨基苯甲酰肼和4-氧代庚二酸的反应研究

张文婷, 孙健, 徐飞, 朱红, 岳瑞雪, 张毅, 钮福祥   

  1. 江苏徐州甘薯研究中心 中国农业科学院甘薯研究所 徐州 221131
  • 收稿日期:2017-06-14 修回日期:2017-08-17 发布日期:2017-09-08
  • 通讯作者: 钮福祥 E-mail:niufuxiang@sina.com
  • 基金资助:

    国家现代农业产业技术体系建设专项资金(No.CARS-10-B20)资助项目.

Reactions of 2-Aminobenzohydrazide and 4-Oxo Pimelic Acid Catalyzed by Iodine in Ionic Liquids

Zhang Wenting, Sun Jian, Xu Fei, Zhu Hong, Yue Ruixue, Zhang Yi, Niu Fuxiang   

  1. Jiangsu Xuzhou Sweetpotato Research Center, Sweet Potato Research Institute, Chinese Academy of Agricultural Sciences, Xuzhou 221131
  • Received:2017-06-14 Revised:2017-08-17 Published:2017-09-08
  • Contact: 10.6023/cjoc201706015 E-mail:niufuxiang@sina.com
  • Supported by:

    Project supported by the Earmarked Fund for the China Agriculture Research System (No. CARS-10-B20).

研究了以2-氨基苯甲酰肼和4-氧代庚二酸为原料,以离子液体为绿色溶剂,在碘催化下进行的反应.结果显示,当酰肼中与酰胺基相连上的N原子没有取代基时,会顺利构建三个新环生成哒嗪并[6,1-b]吡咯并[1,2-a]喹唑啉-1,6,9(7H)-酮衍生物,并通过X单晶衍射分析验证了产物2,3,4,5-四氢化-1H,9H-哒嗪并[6,1-b]吡咯并[1,2-a]喹唑啉1,6,9(7H)-三酮(3a)的结构.而当其取代基是芳基时,由于位阻效应,哒嗪环并没有如期关环,生成四氢吡咯并[1,2-a]喹唑啉-3a(1H)-丙酸衍生物.该方法具有合成路线简洁、溶剂绿色环保、操作简便且收率较高等优点.

关键词: 2-氨基苯甲酰肼, 4-氧代庚二酸, 哒嗪并[6,1-b]吡咯并[1,2-a]喹唑啉-1,6,9(7H)-酮, 四氢化吡咯并[1,2-a]喹唑啉-3a(1H)-丙酸, 离子液体, 空间位阻

The reactions between 2-aminobenzohydrazide and 4-oxopimelic acid catalyzed by iodine using ionic liquids as green solvents were studied. The results showed that when there was no substituents on N atoms attached to amide group of the hydrazide, it will successfully constructed three new rings and formed pyridazino[6,1-b]pyrrolo[1,2-a]quinazoline-1,6,9(7H)-trione derivatives. The structure of 2,3,4,5-tetrahydro-1H,9H-pyridazino[6,1-b]pyrrolo[1,2-a]quinazoline-1,6,9(7H)-trione (3a) was confirmed by X-ray diffraction analysis. However, when the substituents were aryl groups, the pyridazine ring did not closed as expected due to the steric hindrance, and gave tetrahydropyrrolo[1,2-a]quinazolin-3a(1H))-propionic acid derivatives. The advantages of this approach were the simplicity of the synthesis route, environmental protection, easy operation and high efficiency.

Key words: 2-aminobenzohydrazide, 4-oxopimelic acid, pyridazino[6,1-b]pyrrolo[1,2-a]quinazoline-1,6,9(7H)-trione, tetrahydropyrrolo[1,2-a]quinazolin-3a(1H)-propionic acid, ionic liquid, steric hindrance