Corpaverine関連化合物の合成研究(第2報) : 1-(p-Methoxybenzyl)-2-methyl-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-7-olの合成 : 複素環式化合物の合成研究第140報

概要

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Refluxing of 1-(p-methoxybenzyl)-6,7,8-trimethoxy-3,4-dihydroisoquinoline (I) in 20% hydrochloric acid for 5 hours resulted in demethylation of the 7-position, with oxidation of the methylene in the benzyl group in 1-position, affording 1-(P-methoxybenzoyl)-6,8-dimethoxy-7-hydroxy-3,4-dihydroisoquinoline (II). Reduction of II gave III, whose methylation produced IV, confirming the structure of II. In order to prove demethylation of the 7-position in I, the amine (X) was prepared from methyl 3,5-dimethoxy-4-benzyloxybenzoate (V) via VI, VII, VIII, and IX, Schotten-Baumann reaction of X gave the amide (XI), which was cyclized and debenzylated. The final product of this reaction was identified with II by mixed fusion.
公益社団法人日本薬学会の論文
1966-04-25