锡粉促进下α-酰肼基-β-联烯酸乙酯的合成  

The synthesis of ethyl ester ofα-hydrazide-β-dienoate promoted by tin powder

作　　者：张学清 宋义乐 刘伟 ZHANG Xue-qing;SONG Yi-le;LIU Wei(University and College Key Lab of Natural Product Chemistry and Application in Xinjiang,School of Chemistry and Chemical Engineering,Yili Normal University,Yining 835000,China)

机构地区：[1]伊犁师范大学化学化工学院,新疆普通高等学校天然产物化学与应用重点实验室,新疆伊宁835000

出　　处：《化学研究与应用》2025年第2期373-379,共7页Chemical Research and Application

基　　金：伊犁师范大学校级一般基金项目(2021YSYB081)资助。

摘　　要：锡粉可以原位生成有机锡试剂后直接参与反应,不仅避免了有机锡试剂繁琐的制备过程和使用剧毒有机锡试剂,也极大地提高了原子利用率。本文在锡粉存在下,探索了乙醛酸乙酯、酰肼和1-溴-2-丁炔的“一锅法”反应。结果发现,在四氢呋喃为反应溶剂时,以中等至良好的产率获得了2-(2-芳甲酰肼基)-3-甲基-3,4-戊二烯酸乙酯类化合物(4a~4k)。所得化合物的结构经1H NMR,^(13)C NMR,HR-MS(ESI)和IR表征。该产物在医药和合成中具有一定的潜在应用价值。Tin powder can directly participate in the reaction after generating organotin reagent in situ,which not only avoids the cumbersome preparation process of organotin reagent and the use of highly toxic organotin reagent,but also greatly improves the utilization rate of atoms.In this paper,the"one-pot method"reaction of ethyl glyoxylate,hydrazide and 1-bromo-2-butyne were explored in the presence of tin powder.The results showed that 2-(2-arylhydrazide)-3-methyl-3,4-pentadienoic acid ethyl esters(4a~4k)were obtained in medium to good yields when tetrahydrofuran was used as the reaction solvent.The structures of the resulting compounds were characterized by~1H NMR,^(13)C NMR,HR-MS(ESI)and IR.The product had certain potential application value in medicine and synthesis.

关 键 词：锡粉 乙醛酸乙酯 酰肼 一锅法 2-(2-芳甲酰肼基)-3-甲基-3 4-戊二烯酸乙酯 

分 类 号：O621.3[理学—有机化学]