吡咯-2-甲酸酯的一步合成法  

One-step Synthesis of Pyrrole-2-carboxylic Acid Esters

作　　者：张学辉[1] 李松[2] 钟武[2] 吴久鸿[1] 

机构地区：[1]解放军306医院药学部,北京100101 [2]军事医学科学院毒物药物研究所,北京100850

出　　处：《解放军药学学报》2013年第1期23-25,共3页Pharmaceutical Journal of Chinese People's Liberation Army

基　　金：国家自然科学基金;No.81141113

摘　　要：目的研究吡咯-2-甲酸酯的一步合成法。方法尝试在不同的傅-克酰化条件下,新蒸馏的吡咯与氯甲酸酯反应一步制备吡咯-2-甲酸酯。结果优选出了一个通用的反应条件。路易斯酸催化剂使用温和的AlCl3-CH3NO2混合体系。溶剂为1,2-二氯乙烷。反应在冰浴中进行。应用该条件该合成了8个吡咯-2-甲酸酯衍生物。化合物结构经1H-NMR、13C-NMR、IR、MS、HRMS确证。结论本文首次报道了吡咯-2-甲酸酯的一步合成通法;该方法操作简单、条件温和、产率可观。Objective To study a one-step synthesis method of pyrrole-2-carboxylic acid esters. Methods Under different Friedel-Crafts acylation conditions, newly redistillated pyrrole was treated with chloroformic esters to prepare pyrrole-2-carboxylic acid esters in one step. Chloroformic esters were used as carbalkoxylation agents. Sev- eral Friedel-Crafts acylation conditions, including lewis acid catalysts, solvents and temperature, were investigated in succession to find proper conditions for the earbalkoxylation of pyrrole. Results A general reaction condition was preferred. The moderate activity catalyst aluminium trichloride-nitromethane was proved to be more suitable for this reaction. Commonly used solvents for Friedel-Crafts acylation, such as 1,2-dichloroethane, were applicable to this approach. A ice bath was usually necessary to absorb the reaction heat. Eight pyrrole-2-carboxylic acid esters were synthesized in good yields, and their structures were characterized by I H-NMR,13 C-NMR, IR, MS and HRMS. Conclusion A one-step synthesis method of pyrrole-2-earboxylic acid esters was reported for the first time in this pa- per. This method has the advantages of simple operation, mild reaction condtions and good yield.

关 键 词：吡咯-2-甲酸酯 一步合成 氯甲酸酯 傅-克酰化 

分 类 号：R914[医药卫生—药物化学]