(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

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进一步构造了金属冠醚体系.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.

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 ）-H4 shcpa ） .A metallacrown system was then formed by reaction with FeCl3· 6H2O.The ligand was esterified and transformed into （Z）-ethyl 3-（salicylhydrazinocarbonyl） propenoate （（Z）-H3 eshcp） through internal self-catalytic reaction.The metallacrown can be treated with SnCl 2/HCl to obtain purified ester （ Z）-H3 eshcp in good yield .The structure of these compounds were characterized by IR , 1 H-NMR, 13 C-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 .