Chinese Journal of Organic Chemistry >
Synthesis of 4, 5-Dihydropyrrole from γ-Nitro-nitrile
Received date: 2019-05-14
Online published: 2019-07-17
Supported by
the Natural Science Foundation of Shaanxi Province(2009JM2011)
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.
Ting Wen , Meng Kang , Zhanguo Chen . Synthesis of 4, 5-Dihydropyrrole from γ-Nitro-nitrile[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 3162 -3168 . DOI: 10.6023/cjoc201905031
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