Вид документа : Статья из журнала Шифр издания : 54/C 47 Автор(ы) : Charushin V. N., Van der Plas H. C. Заглавие : Ring transformations in reactions of heterocyclic compounds with nucleophiles. The conversion of 5-nitropyrimidine into pyridine derivatives by CH-acitve nitriles Место публикации : Recueil des Travaux Chimiques des Pays-Bas. - 1983. - Vol. 102, № 7-8. - С. 373-377 Примечания : Bibliogr. : p. 377 (19 ref.) ББК : 54 Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ Ключевые слова (''Своб.индексиров.''): 5-nitropyrimidines--ch-acitve nitriles Аннотация: Nitriles R–CH2CN where R is CN, SO2C6H5, C6H4-NO2-p, C6H4-CF3-m, are effective reagents for converting 5-nitropyrimidine (1) into 2-amino-5-nitro-3-R-pyridines (7). In reactions of 1 with cyanoacetic acid derivatives (methyl, ethyl, tert-butyl esters), 3-cyano-5-nitro–2(1H)-pyridone is formed in addition to 7. Ketonic nitriles, such as 3-oxobutyronitrile and 3-oxo–3-phenylpropionitrile, react with 1 to form 2-methyl- and 2-phenyl-5-nitro-3-cyanopyridine, respectively. Plausible mechanisms are discussed. The reaction of 1 with N-(cyanoacetyl)carbamate provides a facile synthetic route to 1,2,3,4-tetrahydro-6-nitropyrido[2,3-d]pyrimidine-2,4-dione. Доп.точки доступа: Van der Plas, H. C.