Ethene-1,1,2,2-tetracarbonitrile and Methanol in the Methylating Reaction of Tertiary Amines to the Quaternary Ammonium Compounds of 1,1-Dicyano-2-methoxy-2-oxoethane-1-ide

作者: Vladimir Р Sheverdov , Vera V Davydova , Oleg E Nasakin , Maksim A Mar’yasov , Olga A Lodochnikova

DOI: 10.1055/S-0037-1610343

关键词: PyridineCounterionMedicinal chemistryAmmonium compoundsChemistryIsonicotinamideMethanolTriethylamineSingle stageCrystal structure

摘要: We discovered a new method to methylate tertiary amines such as urotropine, triethylamine, pyridine, 2-methylpyridine, 4-acetylpyridine, and isonicotinamide, up quaternary ammonium compounds, with 1,1-dicyano-2-methoxy-2-oxoethane-1-ide being the counterion. Methyl-1,3,5,7-tetraazaadamantan-1-ium 1,1-dicyano-2-methoxy-2-oxoethane-1-ide, N,N-diethyl-N-methylethanaminium substituted-methylpyridinium 1,1-dicyano-2-methoxy-2-oxoethane-1-ides were synthesized. Quaternary compounds of 1,1-dicyano-2-methoxy-2-oxothane-1-ide synthesized within single stage by stirring methanol solutions ethene-1,1,2,2-tetracarbonitrile (ETCN) at room temperature. In reaction ETCN in methanol, processes occur that form fragment simultaneous N-methylation. Crystal structures based on X-ray diffraction analysis obtained studied.

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