Studies on Acetylenic Compounds. XLIV. Synthesis of 3-Aminoisoxazoles and 3-Hydroxyisoxazoles (3-Isoxazolones)
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概要
- 論文の詳細を見る
β-Bromocinnamonitrile and hydroxylamine afforded 3-amino-5-phenylisoxazole in the presence of alkali, unexpectedly. So the reaction of acetylenic nitriles and esters with hydroxylamine was examined under alkaline conditions. Phenylpropiolonitrile and propiolonitrile gave 3-amino-5-phenylisoxazole and 3-aminoisoxazole, respectively. Tetrolonitrile afforded a 3 : 1 mixture of 3-amino-5-methyl- and 3-methyl-5-amino-isoxazole in the presence of alkali. Under neutral conditions these nitriles gave the corresponding 5-aminoisoxazoles. Similarly, 3-hydroxy-, 3-hydroxy-5-methyl- and 3-hydroxy-5-phenyl-isoxazole were obtained from the corresponding acetylenic esters. In the case of methyl tetrolate, two isomers of tetrolohydroxamic acid were isolated as the intermediate. On the other hand, free phenylpropiolic acid gave only 3-phenyl-5-isoxazolone under the same alkaline conditions.
- 社団法人日本薬学会の論文
- 1966-11-25
著者
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岩井 一成
Central Research Laboratories, Sankyo Co., Ltd.
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中村 紀雄
New Lead Research Laboratories:sankyo Co. Ltd.
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中村 紀雄
Central Research Laboratories, Sankyo Co., Ltd.
-
岩井 一成
Central Research Laboratories Sankyo Co. Ltd.
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