Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3191-3197.DOI: 10.6023/cjoc201706015 Previous Articles     Next Articles

Articles

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 出版日期:2017-12-25 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 Online:2017-12-25 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).

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