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3-芳胺基丁-2-烯酸酯和酰胺的无溶剂合成与表征

Synthesis and Characterization of Esters and Amides of 3-Arylaminobut-2-enoic Acid via Solvent-free Condensation
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摘要 β-酮基丁酸酯和N-芳基取代的β-酮基丁酰胺通过双乙烯酮与ROH(R=烷基或芳基)或N-甲基苯胺的反应以及乙酰乙酸乙酯的芳胺解反应制备得到。两类化合物与2~3倍物质的量的芳香胺在无溶剂条件于室温下以质子酸为催化剂反应,以中高收率得到一系列的目标化合物,并对它们进行了1HNMR、13CNMR、IR和ESI-MS表征。其中两个还通过X-射线单晶衍射测定了其分子结构。实现了此类化合物无溶剂无金属催化条件下的简单合成。 Acetylacetic esters and N-aryl acetylacetamides were synthsized by the reaction of diketene with alcohols or N-methylaniline and by treatment of ethyl acetylacetate with arylamines,respectively.The title compounds were obtained in moderate to high yield by facial condensation of acetylacetic esters and N-aryl acethlacetamide with 2 ~ 3 folds of various arylamines catalyzed by concentrate protic acid at room temperature and in solvent-free condition.The samples were readily purified by recrystallization or by column chromatolography,and were confirmed by1 HNMR,13 CNMR,IR and ESI-MS.The crystal structures of two compounds were determined by X-ray single crystal diffraction analysis.A simple synthesis method of such compounds under solvent-free and metal-free catalysis was achieved.
作者 鲁赟 崔亮 孙志明 雷珺宇 义建军 肖勇 胥明亮 庄俊鹏 郝海军 LU Yun;CUI Liang;SUN Zhi-ming;LEI Jun-yu;YI Jian-jun;XIAO Yong;XU Ming-liang;ZHUANG Jun-peng;HAO Hai-jun(College of Science,Beijing University of Chemical Technology,Beijing 100029,China;Key Laboratory of Synthetic Resin,Petrochemical Research Institute,PetroChina Company Limited,Beijing 102206,China;Fushun Petrochemical Company,PetroChina Company Limited,Fushun 113008,China)
出处 《化学试剂》 CAS 北大核心 2019年第3期274-282,共9页 Chemical Reagents
基金 中国石油天然气股份有限公司石油化工研究院科研项目(PRIKY16018)
关键词 无溶剂反应 酸催化 Β-二羰基化合物 [N O]配体 缩合反应 双乙烯酮 solvent-free reaction acid catalytic β-dicarbonyl compounds [N,O]ligand condensation diketene
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