摘要
以环己酮为起始原料,经缩合、酰化及酸性水解反应制得2-乙酰基环己酮(1);在三乙烯二胺催化下,1与氰基乙酰胺环化得四氢异喹啉酮(2)和四氢喹啉酮(3)混合物,在乙醇中回流并趁热过滤进行分离纯化得2和3; 2经催化加氢反应合成1-甲基-5,6,7,8-四氢异喹啉酮-4-甲胺,3步总收率39.8%,其结构经1H NMR、13C NMR、1H-15N HMBC和MS确证。
2-Acetyl-cyclohexanone(1) was prepared by condensation,acylation and acidic hydrolysis reaction using cyclohexanone as the starting material.The mixture of 1-methyl-3-oxo-2,3,5,6,7,8-hexahydro-isoquinoline-4-carbonitrile(2) and 4-methyl-2-oxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile(3) were obtained by reaction of 2-cyano-acetamide with 1 in ethanol,using 1,4-diaza-bicyclo[2.2.2]octane as base.2 was separated from 3 by reflux in ethanol and filtration,and then hydrogenated in methanol catalyzed by Raney nickel to afford 1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile with total yield of 39.4%.The structure was confirmed by ~1H NMR,~(13)C NMR,~1H-~(15)N HMBC and MS.
引文
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