クマリン誘導体の研究 (第14報)

β-ナフトクマリンの位置異性体イソ-β-ナフトクマリン及びその4-メチル誘導体について

抄録

Introduction of an aldehyde group into 5, 6, 7, 8-tetrahydro-2-naphthol by the Gatter-mann, Reimer-Tiemann, and Duff reactions is effected at 1-positions, as would be expected from the Mills-Nixon effect, but is contrary to that effect by the Pechmann reaction, condensation taking place at 3-position to afford 6, 7, 8, 9-tetrahydro-2H-naphtho[2, 3-b]pyran-2-one and its 4-methyl derivative. Dehydrogenation of these compounds afforded naphthocoumarin and its 4-methyl derivative possessing anthracene-like structure which are the position isomers of β-naphthocoumarin, with known phenanthrene-like structure. The compound was therefore named iso-β-naphthocoumarin. The structures of β-naphthocoumarin and its 1-methyl derivative and iso-β-naphthocoumarin and its 4-methyl derivative were discussed together with their ultraviolet absorption spectra and velocity of alkaline hydrolysis.