Reductive Oxygenation(第1報) : 3-Methyl-2,3,4,5,6,7-hexahydro-8H-2,6-methanobenzo[d]-1,3-oxazocineの合成 : 複素環式化合物の合成研究第180報

概要

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Reduction of 1-methyl-4-(2-hydroxyethyl)-3,4-dihydrocarbostyril (VIII) by the Ladenburg method or with lithium aluminum hydride afforded the objective cyclized product, 3-methyl-2,3,4,5,6-7-hexahydro-8H-2,6-methanobenzo[d]-1,3-oxazocine (IX), whose catalytic reduction or reduction with lithium aluminum hydride gave 1-methyl-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline (X). IX was also obtained on the reduction of 1-methyl-4-methoxycarbonylmethyl-3,4-dihydrocarbostyril (VII) with lithium aluminum hydride. The same Ladenburg reduction of VIII or its reduction with lithium aluminum hydride did not afford the expected cyclization product (XIV) but produced 4-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline (XIII). It is interesting that a six-membered ring lactam like VII and VIII underwent reductive cyclization to form oxygen-containing heterocyclic compound with Ph-N-C-O-skeleton.
公益社団法人日本薬学会の論文
1967-05-25