有机化学 ›› 2012, Vol. 32 ›› Issue (12): 2309-2314.DOI: 10.6023/cjoc201207027 上一篇    下一篇

研究论文

甲亚胺叶立德的1,3-偶极环加成反应合成螺吲哚里西啶类化合物

李筱芳, 易荣琼, 刘彬, 李志奎, 于贤勇, 易平贵   

  1. 湖南科技大学理论化学与分子模拟省部共建教育部重点实验室 分子构效关系湖南省普通高等学校重点实验室 湖南科技大学化学化工学院 湘潭 411201
  • 收稿日期:2012-07-19 修回日期:2012-08-08 发布日期:2012-08-21
  • 通讯作者: 易平贵 E-mail:pgyi@hnust.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 20971041, 21172066)资助项目.

Synthesis of Novel Spiro Indolizidine Derivatives via 1,3-Dipolar Cycloaddition of Azomethine Ylide

Li Xiaofang, Yi Rongqiong, Liu Bin, Li Zhikui, Yu Xianyong, Yi Pinggui   

  1. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201
  • Received:2012-07-19 Revised:2012-08-08 Published:2012-08-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20971041, 21172066).

通过7-芳亚甲基-6,7-二氢中氮茚-8(5H)-酮与甲亚胺叶立德(经苊醌或靛红与肌氨酸反应原位生成)进行的l,3-偶极环加成反应, 合成了具有良好产率的新的1'-甲基-4'-芳基-5",6"-二氢-2H,8"H-二螺[苊烯-1,2'-吡咯烷-3',7"-中氮茚]-2,8"-二酮类化合物和1'-甲基-4'-芳基-5",6"-二氢-1H,8"H-二螺[吲哚-3,2'-吡咯烷-3',7"-中氮茚]-2,8"-二酮类化合物. 采用NMR, IR, 质谱, 元素分析以及X射线单晶衍射等多种谱学技术对产物进行了结构表征.

关键词: 螺杂环, 1,3-偶极环加成, 甲亚胺叶立德, 靛红, 苊醌

The 1,3-dipolar cycloaddition of azomethine ylide generated in situ from acenaphthenequinone (isatin) and sarcosine to 7-arylmethylidene-6,7-dihydroindolizin-8(5H)-ones afforded novel 4'-aryl-1'-methyl-5'',6''-dihydro-2H,8''H- dispiro[acenaphthylene-1,2'-pyrrolidine-3',7''-indolizine]-2,8''-diones and 4'-aryl-1'-methyl-5'',6''-dihydro-8''H-dispiro[indole-3,2'-pyrrolidine-3',7''-indolizine]-2,8''(1H)-diones in moderate yields. The structures of the products were characterized thoroughly by NMR, IR, MS, elemental analysis together with X-ray crystallographic analysis.

Key words: spiroheterocycle, 1,3-dipolar cycloaddition, azomethine ylides, isatin, acenaphthenequinone