由γ-硝基腈合成4,5-二氢吡咯衍生物  

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

作　　者：文婷 康梦 陈战国[1] Wen Ting;Kang Meng;Chen Zhanguo(Key Laboratory of Macromolecular Science of Shaanxi Province,School of Chemistry and Chemical Engineering,Shaanxi Normal University,Xi'an 710119)

机构地区：[1]陕西师范大学化学化工学院陕西省大分子科学重点实验室

出　　处：《有机化学》2019年第11期3162-3168,共7页Chinese Journal of Organic Chemistry

基　　金：陕西省自然科学基金(No.2009JM2011)资助项目~~

摘　　要：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.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.

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 

分 类 号：O62[理学—有机化学]