SYNTHESIS AND PROPERTIES OF 6-METHYL-4-(m-NITROPHENYL)-3-CYANOPYRIDIN-2(1H)-ONES, THE CORRESPONDING PYRIDINE-2(1H)-THIONES, AND THEIR HYDROGENATED ANALOGS

Article abstract of DOI:10.1007/BF00515580

The condensation of 4-pyridylacetone, m-nitrobenzaldehyde, and cyanoacetamide (cyanothioacetamide) in the presence of bases was used to obtain 5-pyridyl-substituted 6-methyl-4-(m-nitrophenyl)-3-cyanopyridin-2(1H)-ones, the corresponding pyridine-2(1H)-thiones, and their hydrogenated analogs. 2-Carbamoylmethylthiopyridine was isolated in the alkylation of 5-(4'-pyridyl)pyridine-2(1H)-thione with iodoacetamide under mild conditions, while 2-carbamoylthio-5-(N-carbamoylmethyl-4'-pyridyl)pyridine iodide was isolated under more severe conditions.