Reaction of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with aromatic aldehydes afforded the corresponding Schiff bases, the reduction of which with sodium borohydride led to the formation of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones. Acylation of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with chloroacetyl chloride resulted either in the corresponding chloroacetamides or in 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones. A possibility to form octahedral complex with calcium chloride was demonstrated by the example of 3-(benzylamino)-6-methyl-4-phenylpyridin-2(1H)-one. Structure of all the prepared compounds was proved by 1H and 13C NMR spectroscopy, as well as single crystal X-ray diffraction method. Among a series of novel compounds, 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-one derivatives showed antiradical activity against DPPH and ABTS radicals.