I. Iwai, N. Nakamura
Nov 25, 1966
Citations
0
Influential Citations
36
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
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.