C 47 Charushin, V. N. Ring transformations in reactions of heterocyclic compounds with nucleophiles. The conversion of 5-nitropyrimidine into pyridine derivatives by CH-acitve nitriles [Electronic resource] / V. N. Charushin, H. C. Van der Plas // Recueil des Travaux Chimiques des Pays-Bas. - 1983. - Vol. 102, № 7-8. - P373-377. - Bibliogr. : p. 377 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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. \\\\expert2\\nbo\\Recueil des Travaux Chimiques des Pays-Bas\\1983. V. 102, N 7-8. P. 377.pdf |