1-Methyl-3-acetyl-6,7-dimethoxyisoquinolineの合成 : 複素環式化合物の合成研究第131報

概要

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In order to examine the nature of acetyl group bonded directly to the isoquinoline ring, 3,4-dihydrolsoquinolines (V) and 1,2,3,4-tetrahydroisoquinolines (VI) were prepared from vanillin by the usual method. Condensation of these compounds with ethyl acetate, in the presence of sodium hydride, and ketonolysis of their products unexpectedly afforded the dehydrogenated 1-methyl-3-acetyl-6,7-dimethoxyisoquinoline (X) instead of IX, from V. In the case of VI compounds, majority of them produced X and formation of XII was not detected. In order to prove the formation of X, V was dehydrogenated to XIII and submitted to ketonolysis through XIV under the same conditions as above. The product X thereby obtained showed no depression of the melting point when fused with the foregoing product.
公益社団法人日本薬学会の論文
1966-01-25