置換レゾルシン類の還元 (第1報)

4-Benzamidocyclohexane-1,3-dioneとその関連化合物の合成

抄録

Tetracyclines have remarkable antibacterial action and, under the assumption that the A-ring characteristic to tetracyclines might be responsible for this activity, it seemed of interest to synthesize this A-ring and similar compounds, and to examine relationship between chemical structure and antibacterial activity. Therefore, 4-benzamidocyclohexane-1, 3-dione (I), a compound with benzamido group attached to 4-position of cyclohexane-1, 3-dione, the fundamental skeleton of the A-ring in tetracyclines, was syntheized by catalytic alkaline reduction of 2, 4-dihydroxybenz-anilide. During this reduction, it was found that difficulty reduced compounds can easily be reduced by suitably adjusting the alkalinity. Further, the enol ethyl ether (II) and 3-amino compounds of (I) were prepared and they were found to still retain the dione groups, through analytical values and from ultraviolet and infrared absorption spectra.