YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
複素環式化合物の合成研究(第175報) : 1-(α-Hydroxy-4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-5-olの合成
亀谷 哲治加納 慎蔵渡辺 四男也菊池 豊彦
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1967 年 87 巻 4 号 p. 406-409

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2-Benzyloxy-3, 4-dimethoxyphenethylamine (VIII) was synthesized from 2-benzyloxy-3, 4-dimethoxybenzaldehyde (VI) via ω-nitrostyrene derivative (VII) by the conventional method and condensation of VIII with p-methoxyphenacetyl chloride gave the amide (IX). The Bischler-Napieralski reaction of IX afforded the 3, 4-dihydroisoquinoline base but this was unexpectedly found to be the oxidation product (XI). Treatment of XI with methyl iodide, followed by reduction with sodium borohydride to the O-benzyl derivative (XII), and its debenzylation afforded the title compound (XIII).
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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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