Coreximine関連化合物の合成研究(第3報) : Eschweiler-Clarke反応条件下におけるCoreximineの位置異性体の生成 : 複素環式化合物の合成研究第164報

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The 3,4-dihydroisoquinoline compound (XII), obtained by the Bischler-Napieralski reaction of the amide (XI), was derived to the 1,2,3,4-tetrahydroisoquinoline compound (XIII) and debenzylated to 1-(4-hydroxy-3-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol (II). The free base of XII was very labile and easily changed to 1-benzoylisoquinoline (XIV) which was submitted to the Clemmensen reduction to obtain II. In order to obtain 1-(4-hydroxy-3-methoxybenzyl)-6-methoxy-2-methyl-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (I), II was submitted to the Eschweiler-Clarke reaction and an unexpected cyclization to the dibenzoquinolizine base occurred, forming XV, a kind of isomer of coreximine. Methylation of XV with diazomethane gave (±)-norcoralydine (XVI), while treatment of II with sodium borohydride and formaldehyde solution resulted in normal N-methylation to form I.
公益社団法人日本薬学会の論文
1967-02-25