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  

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

作　　者：张文婷 孙健[1] 徐飞[1] 朱红[1] 岳瑞雪[1] 张毅[1] 钮福祥[1] 

机构地区：[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

出　　处：《有机化学》2017年第12期3191-3197,共7页Chinese Journal of Organic Chemistry

基　　金：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~~

摘　　要：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.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（7 H）-trione derivatives. The structure of 2,3,4,5-tetrahydro-1 H,9 H-pyridazino[6,1-b]pyrrolo[1,2-a]quinazoline-1,6,9（7 H）-trione（3 a） 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-3 a（1 H））-propionic acid derivatives. The advantages of this approach were the simplicity of the synthesis route, environmental protection, easy operation and high efficiency.

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 

分 类 号：O621.251[理学—有机化学]