含窒素複素環化合物の研究(第35報)4-Amino-2-cyano-1,3-dimethoxy-1,2,3,4-tetrahydroisoquinoline類の合成とそれらの還元反応について

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Reaction of 4-bromo-2-cyano-1,3-dimethoxy-1,2,3,4-tetrahydroisoquinoline with aniline (or diethylamine), in the presence of a phase-transition catalyst, results in fascile formation of 4-anilino (or diethylamino)-2-cyano-1,3-dimethoxy-1,2,3,4-tetrahydroisoquinoline. Application of sodium borohydride to this compound in ethanol afforded 4-anilino (or diethylamino)-2-methyl-1,2,3,4-tetrahydroisoquinoline in a high yield. Use of methylmagnesium iodide in place of sodium borohydride produced 4-anilino-2-cyano-1-methyl-1,2-dihydroisoquinoline and 4-anilino-1-methylisoquinoline. It was clarified from these products that the reduction of N-C≡N group passed through a diaminomethane derivative.
公益社団法人日本薬学会の論文
1979-06-25