Citation: Wen Ting, Kang Meng, Chen Zhanguo. Synthesis of 4, 5-Dihydropyrrole from γ-Nitro-nitrile[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3162-3168. doi: 10.6023/cjoc201905031 shu

Synthesis of 4, 5-Dihydropyrrole from γ-Nitro-nitrile

Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119

Corresponding author: Chen Zhanguo, chzhg@snnu.edu.cn
Received Date: 14 May 2019
Revised Date: 28 June 2019
Available Online: 17 November 2019
Fund Project: Project supported by the Natural Science Foundation of Shaanxi Province (No. 2009JM2011)the Natural Science Foundation of Shaanxi Province 2009JM2011

Figures(4)

A new method for the synthesis of 4, 5-dihydropyrrole derivatives from γ-nitro-nitriles is described. In this procedure, the nitro groups of nitro-nitriles were reduced into aminoes under Fe+HCl systerm in methanol at 30℃ firstly. And then the amino-groups reacted with cyano groups to form target compounds via intramolecular nucleophilic addition reaction and rearrangement reaction. Under the optimized conditions, all γ-nitro-nitriles can be easily converted into 4, 5-dihydropyrrole derivatives in satisfactory yield. It shows that the reaction has better universality. Based on the experimental results, the possible reaction mechanism was proposed.
- 4, 5-dihydropyrrole derivative,
- γ-nitro-nitrile,
- malonitrile,
- ethyl cyanoacetate
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