Naphthisoxazole誘導体の合成研究(第1報)4,5-Dihydronaphth-[2,1-d]isoxazole誘導体の合成

概要

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Reaction of 2-acyl-1-tetralones with hydroxylamine was carried out. The reaction of 2-methoxalyl-1-tetralones (IIa-d) with hydroxylamine hydrochloride in methanol gave the cyclized compounds, 3-methoxycarbonyl-4,5-dihydronaphth[2,1-d]isoxazoles (IIIa-d), which were converted to the corresponding 2-cyano-1-tetralones (Va-d) under alkaline conditions. The reaction of 2-acetyl-1-tetralones (IIe, f) with hydroxylamine hydrochloride gave 3-methyl-4,5-dihydronaphth[2,1-d]isoxazo1es (IIIe, f). IIIa, c were reduced by LiAlH_4 or NaAlH_2(OCH_2CH_2OCH_3)_2 to 3-hydroxymethyl-4,5-dihydronaphth-[2,1-d] isoxazoles (VIa, c), which, on treatment with PCl_5,gave 3-chloromethyl-4,5-dihydronaphth[2,1-d]isoxazoles (VIIa, c). Reduction of VIIa, c with zinc dust in acetic acid afforded IIIe, f. When one equivalent of 3-hydroxymethyl-7-methoxy-4,5-dihydronarhth[2,1-d]isoxazo1e (VIc) was allowed to react with 2 equivalents of PCl_5,6-chloro-3-chloromethyl-7-methoxynaphth[2,1-d]isoxazo1e (VIIIc) and VIIc were obtained. The structure of VIIIc was supported by its spectral data.
公益社団法人日本薬学会の論文
1975-07-25