Вид документа : Статья из журнала Шифр издания : 54/K 66 Автор(ы) : Kodess M. I., Sosnovskikh V. Ya., Moshkin V. S. Заглавие : Reactions of 3-(polyfluoroacyl)chromones with hydroxylamine : synthesis of novel R - containing isoxazole and chromone derivatives Место публикации : Tetrahedron. - 2008. - Vol. 64, № 34. - С. 7877-7889: рис. Примечания : Библиогр. : с. 7888-7889 (32 назв.) ББК : 54 Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reaction of 3-(polyfluoroacyl)chromones with hydroxylamine free base proceeds via nucleophilic 1,4-addition followed by opening of the pyrone ring and subsequent cyclization to 4-(polyfluoroalkyl)-4H-chromeno[3,4-d]isoxazol-4-ols in good yields. On treatment with trifluoroacetic acid, the isoxazole ring of this annulated heterocyclic system opens to give 3-cyano-2-(polyfluoroalkyl)chromones, which were successfully hydrolyzed with concentrated H2SO4 to afford 3-carbamoyl-2-(polyfluoroalkyl)chromones. On the other hand, oximation of 3-(polyfluoroacyl)chromones with hydroxylamine hydrochloride occurs either at the carbonyl carbon atom connected to the RF group or at the C-2 atom to give 3-RFC(NOH)-chromones and 5-RF-4-salicyloylisoxazole oximes, respectively. The former were easily converted to 3-RF-4-salicyloylisoxazoles by simple heating in dimethyl sulfoxide.?? Держатели документа: Центральная научная библиотека УрО РАН Доп.точки доступа: Sosnovskikh, V. Ya.; Moshkin, V. S.; Кодесс Михаил Исаакович