SYNTHESIS OF 3-AMINO-6-METHYL-4-PHENYLPYRIDIN-2(1<i>Н</i>)-ONE AND ITS DERIVATIVES

Abstract

A reaction of 2-cyanoacetamide with benzylideneacetone in DMSO containing potassium tert-butoxide was used to synthesize 3-cyano-6methyl-4-phenylpyridin-2(1Н)-one, which was converted by acidic hydrolysis to 6-methyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carboxamide. A Hofmann reaction of this compound in the presence of sodium hypobromite led to 3amino-5-bromo-6-methyl-4phenylpyridin-2(1H)-one, while its treatment with calcium hypochlorite produced 5-methyl-7-phenyloxazolo[5,4-b]pyridin-2(1H)-one. The latter compound was converted by heating with alkali to 3-amino-6-methyl-4-phenylpyridin-2(1Н)-one, which gave azomethine in a reaction with benzaldehyde, while N-acylated derivatives were obtained in reactions with acyl halides. The heating of N¹,N²-bis(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)oxalylamide in the presence of POCl₃ allowed to obtain 5,5'-dimethyl-7,7'-diphenyl-2,2'-bis(oxazolo[5,4-b]pyridine).

Authors: Anton L. Shatsauskas, Anton A. Abramov, Elina R. Saibulina, Irina V. Palamarchuk, Ivan V. Kulakov, Alexander S. Fisyuk*