由γ-硝基腈合成4, 5-二氢吡咯衍生物
收稿日期: 2019-05-14
网络出版日期: 2019-07-17
基金资助
陕西省自然科学基金(2009JM2011)
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)
建立了由γ-硝基腈合成4，5-二氢吡咯衍生物的新方法.用还原铁粉和浓盐酸混合体系作为还原剂，以甲醇为溶剂，γ-硝基腈在30℃下其硝基被还原成氨基，该氨基与分子内的氰基自发地发生亲核加成反应和重排反应，形成一系列4，5-二氢吡咯杂环化合物.在优化条件下，不同结构的γ-硝基腈均能以满意的收率转变成4，5-二氢吡咯衍生物，说明该反应具有较好的普适性.根据实验结果，提出了可能的反应机理.
关键词： 4, 5-二氢吡咯衍生物; γ-硝基腈; 丙二腈; 氰基乙酸乙酯
文婷 , 康梦 , 陈战国 . 由γ-硝基腈合成4, 5-二氢吡咯衍生物[J]. 有机化学, 2019 , 39(11) : 3162 -3168 . DOI: 10.6023/cjoc201905031
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.
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