複素環式化合物の合成研究(第310報) : 1,2,3,4-Tetrahydro-8-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxyisoquinolineおよびDiphenolic 1-Phenethylisoquinoline誘導体の合成とそのPhenol Oxidationの試み
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概要
- 論文の詳細を見る
The Bischler-Napieralski reactiorx of N-(5-benzyloxy-3,4-dimethoxyphenethyl)-2-(3-benzyloxy-4-methoxyphenyl) acetamide (VI) gave a mixture of 3,4-dihydroisoquinolines cyclized in the ortho-and para-position of the 5-benzyloxy group. Without isolation, the mixture was derived to the 1,2,3,4-tetrahydroisoquinoline compounds, and separated into 8-hydroxy (XI) and 6-hydroxy (XII) compounds. The mixture of XI and XII was submitted to the Mannich reaction and the product was methylated with diazomethane to 1,2,3,10,11-pentamethoxyprotoberberine (XIV). The Bischler-Napieralski reaction of N-(5-benzyloxy-3,4-dimethoxyphenethyl)-3-(3-ethoxycarbonyl-4-methoxyphenyl) propionamide (XX) also gave a mixture of 3,4-dihydroisoquinolines which was derived to the 1,2,3,4-tetrahydroisoquinolines and separated into 8-hydroxy (XXIV) and 6-hydroxy (XXV) compounds. Discrimination of 8-and 6-hydroxyisoquinolines was made from infrared and nuclear magnetic resonance spectral data. An attempted synthesis of the so-called 'homocularine' by the phenolic oxidation of the former XXIV, 6,7-dimethoxy-8-hydroxy-1-(4-hydroxy-3-methoxyphenethyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline, did not materialize.
- 社団法人日本薬学会の論文
- 1969-05-25
著者
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菅原 勉
Pharmaceutical Institute, Tohoku University
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福本 圭一郎
東北大・薬
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亀谷 哲治
東北大学医学部薬学科
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菅原 勉
Pharmaceutical Institute Tohoku University
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福本 圭一郎
東北大学医学部薬学科
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菅原 勉
東北大学医学部薬学科
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