複素環式化合物の合成研究(第151報) : 3,4-Dihydro-6,7,8-trimethoxyisoquinolineの選択的脱メチル反応ならびにAnhalamineの改良全合成

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Sythesis of mescaline (V) was examined and high-pressure reduction of IV afforded the compound in a good yield. V was formylated by the usual method and the product (X) was cyclized to 3,4-dihydro6,7,8-trimethoxy-isoquinoline (XI). In order to effect selective demethylation, XI was heated with aluminum trichloride or tribromide in carbon disulfide, or heated for a few hours in conc. hydrochloric acid, by which the phenolic base (XII) was obtained. Reduction of the methiodide (XIII) or XII gave a product which agreed neither with an authentic sample of anhalidine nor with 1,2,3,4-tetrahydro-7,8-dimethoxy-2-methyl-6-isoquinolinol, and it was considered that the demethylation occurred from the methoxyl in 7-position. Therefore, 4-benzyloxy-3,5-dimethoxyphenethylamine (XXVII) was synthesized from XXI via XXVI, and debenzylation of XXIX obtained by cyclization of the formylated product (XXVIII) of XXVII finally afforded the objective XII. This compound was found to be identical with the product (XII) obtained by selective demethylation of XI with hydrochloric acid. Reduction of XVIII with lithium aluminum hydride gave anhalamine (XIX) directly, without passing through XVIIIa.
公益社団法人日本薬学会の論文
1966-10-25