高等学校化学学报 ›› 1982, Vol. 3 ›› Issue (2): 210-216.

• 论文 • 上一篇    下一篇

4-甲酰基-2,2,5,5-四甲基四氢呋喃-3-酮与胺的缩合产物及其性质

于振华, 尹承烈   

  1. 北京师范大学化学系
  • 收稿日期:1980-12-17 出版日期:1982-04-24 发布日期:1982-04-24

THE PREPARATIONS AND REACTIONS OF THECONDENSED PRODUCTS FROM 4-FORMYL-2, 2, 5,5-TETRAMETHYL-TETRAHYDRO-3-FURANONE

Yu Zhenhua, Yin Chcnglie   

  1. Department of Chemistry, Beijing Normal University, Beijing
  • Received:1980-12-17 Online:1982-04-24 Published:1982-04-24

摘要: 全取代的呋喃酮[Ⅰ]易与胺类发生缩合反应,生成相应的插烯式酰胺,与甲胺在不同溶剂中可得单分子或双分子缩合产物。这类缩合产物不能用碘甲烷,重氮甲烷甲基化;用过氧化氢氧化得到少一碳原子的二元酸;与乙酰乙酸乙酯作用生成吡啶衍生物;与格氏试剂作用,发生类似于α,β-不饱和羰基化合物的1,4-加成反应,生成产物业经合成方法证明。

Abstract: The fully substituted furanone [I] condensed easily with amines to form the corresponding products, and in the case of methyamine, depending on the solvent used, gave the mono- or bimolecular furanone condensed products. These products were readily hydrolysed in aqueous acids, regenerating the amines and [I].All the condensed products obtained could not be methylated with methyl iodide or diazomethane, due to the presence of an "inserted ethylenic linkage" in the amide molecule. By oxidation with hydrogen peroxide, a dicarboxylic acid [K] (which less by one methylene group) was obtained, and treating with acetoacetic ester, a derivative of pyridine [V] was formed via the intermediate [VI].Addition of Grignard reagent to condensed products gave 1.4-addition products [IV], which was proved by relevant synthesis.