オキサゾールカルボン酸誘導体の合成(第13報)アミノオキサゾール類の還元的開裂についてその 6 2-Amino-2-oxazoline類の合成と還元的開裂

概要

論文の詳細を見る
2-Amino-4-R_1-5-R_2-2-oxazoline (II) was synthesized by the reaction of amino alcohols (I) with cyanogen bromide. By the acetylation of II, diacetyl derivative (V) was obtained more easily than monoacetyl derivative (IV). Configuration of II was easily presumed from the vicinal coupling constant (JVIC) in the nuclear magnetic resonance spectra of V. V was hydrolysed to 3-acetyl-4-R_1-5-R_2-2-oxazolidone (VI) and 2-acetamido-2-R_1-1-R_2-ethyl acetylcarbamate (VII) with 5% hydrochloric acid at room temperature. The steric structure of VII was confirmed by its conversion to 2-acetamido-2-R_1-1-R_2-ethanol (IX) via 2-acetamido-2-R_1-1-R_2-ethyl carbamate (VIII). In the catalytic reduction of II at room temperature under ordinary pressure, IIa, b was recovered when using palladiumcarbon catalyst in ethanol, and IIa, b gave the corresponding 4-cyclohexyl-II (X) when using platinum oxide in acetic acid. High-pressure reduction of IIa afforded (1-phenylethyl)-urea (XIIa) when using palladium-carbon catalyst, and Xa when using Raney nickel catalyst.
公益社団法人日本薬学会の論文
1977-02-25