オキサゾールカルボン酸誘導体の合成(第7報) : アミノオキサゾール類の還元的開裂についてその1

概要

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In order to examine the reductive cleavage of aminoxazoles, benzyl 5-phenyl-2-oxazolecarbamate (I), 2-amino-5-phenyloxazole (II), and few related compounds were submitted to catalytic reduction at ordinary pressure, using various catalysts, and following observations were made. 1) I is converted to phenethylurea (IV) via II when using palladium-carbon catalyst in ethanol, and via 1-carbobenzyloxy-3-phenethylurea (VI) when using platinum oxide catalyst. However, II is obtained selectively when using palladium-barium sulfate catalyst in ethanol, and VI, when using platinum oxide catalyst in acetic acid. 2) II affords IV when using either palladium-carbon or platinum oxide catalyst in ethanol or acetic acid. 3) Hydrochloric acid promotes ring cleavage but alkali markedly inhibits fission. 4) Raney nickel is inactive as a catalyst in this reaction. 5) Ring cleavage of ethyl 5-phenyl-2-oxazolecarboxylate (IX) and 5-phenyloxazole (X) do not progress under these conditions.
公益社団法人日本薬学会の論文
1967-01-25