1-(3-Hydroxy-4-methoxyphenethyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-6-olおよび1-(3-Hydroxy-4-methoxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-6,8-diolの合成ならびにそのPhenol Oxidationによる閉環の試み : 複素環式化合物の合成研究第228報

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Reaction of phenethylamine (XVII) and a carboxylic acid (XVIII) afforded the amide (XIX) which was converted to the amide (XX) and submitted to the Bischler-Napieralski reaction to prepare the 3,4-dihydroisoquinoline compound (XXI). XXI was converted, via its methiodide (XXII) and 3'-hydroxyisoquinoline compound (XXIV), into 1-(3-hydroxy-4-methoxyphenethyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol (VIII). Another reaction of the amine (XXVII) and a carboxylic acid (XXVIII) afforded the amide (XXIX) whose Bischler-Napieralski reaction gave the 3,4-dihydroisoquinoline compound (XXX), which was converted via its methiodide (XXXI) and the 2-methyl compound (XXXII) into 1-(3-hyrdoxy-4-methoxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol (XI). The amide (XIX) was derived to the secondary amine (XXVI) via the amide (XXV) and debenzylation of XXVI afforded 3,3'-dihydroxyamine (XV). Phenolic oxidative coupling was examined with the compounds so obtained, VIII, XI, and XV, but the reaction did not materialize.
公益社団法人日本薬学会の論文
1968-05-25