Phenylglycidyl Ether誘導体の研究(第4報) : 1-Phenoxy(or o-Substituted Phenoxy)-3-diethylamino-2-propanolの酸化について

概要

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Oxidation of 1-phenoxy-or 1-(2-substituted)phenoxy-3-diethylamino-2-propanols(I) to the corresponding ketones with various reagents was examined. 1) Oxidation of I with hydrogen peroxide or periodic acid resulted in recovery of the starting material. 2) Mild oxidation of I with acidic potassium permanganate afforded a fair amount of amino-ketones, together with cleaved products, phenoxyacetic acid, diethylamine, and carbon dioxide. At the same time, a small amount of bis(1-phenoxy-3-diethylaminopropyl) ether was obtained as the abnormal oxidation product. The presence of a nitro group in the ortho position accelerated the cleavage reaction and o-nitrophenol was isoated in the oxidation of 1-(o-nitrophenoxy)-3-diethylamino-2-propanol. 3) Oxidation with chromium trioxide or potassium dichromate gave result similar to that of permanganate oxidation. 4) Amino-ketones were obtained in a satisfactory yield, without being accompanied by cleavage reaction, by the use of aluminum or potassium tert-butoxide. 5) The amino-ketones were cleaved into phenoxyacetic acid and diethylmethylamine by treatment with alkali hydroxide solution.
公益社団法人日本薬学会の論文
1969-11-25