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
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  • 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

  网络出版日期: 2012-08-21

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
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  • 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 date: 2012-07-19

  Revised date: 2012-08-08

  Online published: 2012-08-21

Supported by

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

摘要

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.

本文引用格式

李筱芳 , 易荣琼 , 刘彬 , 李志奎 , 于贤勇 , 易平贵 . 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[J]. 有机化学, 2012 , 32(12) : 2309 -2314 . DOI: 10.6023/cjoc201207027

Abstract

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.

参考文献

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