Citation: Zhu Meijun, Han Ying, Liu Changzhou, Ma Weiqing, Yan Chao-Guo. 1, 3-Dipolar cycloaddition for selective synthesis of functionalized spiro[indoline-3, 3'-pyrrolizines][J]. Chinese Chemical Letters, ;2020, 31(6): 1554-1557. doi: 10.1016/j.cclet.2019.12.028 shu

1, 3-Dipolar cycloaddition for selective synthesis of functionalized spiro[indoline-3, 3'-pyrrolizines]

Zhu Meijun ^a ,
Han Ying ^b,*, ,
Liu Changzhou ^b ,
Ma Weiqing ^b ,
Yan Chao-Guo ^b,*,

a.
Jianghai Polytechnic College, Yangzhou 225101, China
b.
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China

hanying@yzu.edu.cn

cgyan@yzu.edu.cn

Received Date: 26 September 2019
Revised Date: 17 December 2019
Accepted Date: 19 December 2019
Available Online: 19 December 2019

Figures(6)

The 1, 3-dipolar cycloaddition reaction of dimethyl hex-2-en-4-ynedioate with azomethine ylides derived from reaction of L-proline with various isatins in methanol selectively resulted in the formation of functionalized spiro[indoline-3, 3'-pyrrolizine]acrylates as main products and spiro[indoline-3, 3'-pyrrolizine]propiolates as minor products. This result indicated that the electron-deficient alkyne has higher reactivity than that of electron-deficient alkene in 1, 3-dipolar cycloaddition reaction.
- Azomethine ylide,
- Spirooxindoline,
- L-Proline,
- Electron-deficient alkyne,
- 1, 3-Dipolar cycloaddition reaction
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