金龙飞, 杨 明, 毛 骁, 张 亚.(Z)-3-水杨酰肼羰基丙烯酸乙酯的合成[J].中南民族大学学报自然科学版,2014,(1):11-14
(Z)-3-水杨酰肼羰基丙烯酸乙酯的合成
Synthesis and Characterization of (Z)-Ethyl 3-(Salicylhydrazinocarbonyl) Propenoate
  
DOI:
中文关键词: (Z)-3-水杨酰肼羰基丙烯酸乙酯  合成  表征  内部自催化反应
英文关键词: (Z)-Ethyl 3-(salicylhydrazinocarbonyl) propenoate  synthesis  characterization  internal self-catalytic reaction
基金项目:湖北省自然科学基金资助项目(2008CDA067)
作者单位
金龙飞, 杨 明, 毛 骁, 张 亚 中南民族大学 化学与材料科学学院 武汉 430074 
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中文摘要:
      为进一步探讨双酰肼羧酸酯的合成方法,以水杨酸甲酯和水合肼为原料,首先合成了水杨酰肼,再与顺丁烯二酸酐反应,合成了(Z)-3-水杨酰肼羰基丙烯酸((Z)-H4shcpa).然后由(Z)-H4shcpa和FeCl3?6H2O进一步构造金属冠醚体系.通过内部自催化反应,(Z)-H4shcpa发生酯化,经过SnCl2 / HCl溶液还原体系处理,最终得到了乙酯化的产物(Z)-3-水杨酰肼羰基丙烯酸乙酯((Z)-H3eshcp).对目标化合物进行了IR、1H-NMR、13C-NMR和元素分析等表征.结果表明:通过内部自催化反应,经由金属冠醚体系,可以解决双酰肼羧酸乙酯的合成难题.
英文摘要:
      To obtain a synthesis method of the esterification of carboxylic acid with bis-hydrazide, salicylhydrazide was prepared using methyl salicylate and hydrazine hydrate ,followed by reaction with maleic anhydride to produce (Z)-3-(salicylhydrazinocarbonyl) propenoic acid ((Z)-H4shcpa). A metallacrown system was then formed by reaction with FeCl3?6H2O.The ligand was esterified and transformed into (Z)-ethyl 3-(salicylhydrazinocarbonyl) propenoate ((Z)-H3eshcp) through internal self-catalytic reaction. The metallacrown can be treated with SnCl2 / HCl to obtain purified ester (Z)-H3eshcp in good yield. The structure of these compounds were characterized by IR, 1H-NMR, 13C-NMR and element analysis. It showed that the difficult problem of ethyl-esterification of carboxylic acid with bis-hydrazide can be solved through the internal self-catalytic reaction of metallacrown system.
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