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

doi:10.6023/cjoc201207027

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2309-2314.DOI: 10.6023/cjoc201207027 Previous Articles Next Articles

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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

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

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).

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

Cite this article

Li Xiaofang, Yi Rongqiong, Liu Bin, Li Zhikui, Yu Xianyong, Yi Pinggui. Synthesis of Novel Spiro Indolizidine Derivatives via 1,3-Dipolar Cycloaddition of Azomethine Ylide[J]. Chin. J. Org. Chem., 2012, 32(12): 2309-2314.

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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

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

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