Chem. J. Chinese Universities ›› 1982, Vol. 3 ›› Issue (2): 210.

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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

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.

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