Studies on the Syntheses of 7,8-Disubstituted 1-Benzylisoquinoline and Related Compounds. (4). Synthesis of dl-Cularidine
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概要
- 論文の詳細を見る
Bischler-Napieralski reaction of phenolic bromo amide (VIII), which was obtained from the Schotten-Baumann reaction of 4-benzyloxy-2-bromo-5-hydroxyphenethylamine (VI) with 2-bromo-4,5-dimethoxyphenylacetyl chloride (VII) and then reduction with NaBH_4 of the resultant dihydroisoquinoline (IX) gave 7-benzyloxy-5-bromo-1-(2-bromo-4,5-dimethoxybenzyl)-8-hydroxy-1,2,3,4-tetrahydroisoquinoline(X). N-Methylation of X afforded XI. The Ullmann reaction of XI in the presence of potassium carbonate and cupric oxide in pyridine gave 6-benzyloxy-4-brome-1-methyl-9,10-dimethoxy-1,2,3,12,12a-pentahydrobenzoxepino[2,3,4-i, j]isoquinoline (XII). Subsequent debenzylation and debromination of XII with hydrogen over 10% palladium-charcol gave dl-cularidine (Id) which was identified with natural cularidine by infrared and nuclear magnetic resonance spectral comparisons.
- 公益社団法人日本薬学会の論文
- 1973-05-25
著者
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菊地 豊彦
東京薬科大学
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飯田 英夫
Tokyo College of Pharmacy
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菊地 豊彦
Tokyo College of Pharmacy
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許 弘卿
Tokyo College of Pharmacy
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