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Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A reaction of 2-cyanoacetamide with benzylideneacetone in DMSO containing potassium tert-butoxide was used to synthesize 3-cyano-6-methyl-4-phenylpyridin-2(1H)-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 3-amino-5-bromo-6-methyl-4-phenylpyridin-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(1H)-one, which gave azomethine in a reaction with benzaldehyde, while N-acylated derivatives were obtained in reactions with acyl halides. The heating of N 1,N 2-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).

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The work was performed with financial support from the Russian Foundation for Basic Research (project 15-53- 45084 IND_a).

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Authors and Affiliations

  1. Omsk State Technical University, 11 Mir Ave., Omsk, 644050, Russia

    Anton L. Shatsauskas & Alexander S. Fisyuk

  2. Omsk State University named after F. M. Dostoevsky, 55a Mir Ave., Omsk, 644077, Russia

    Anton A. Abramov, Elina R. Saibulina, Irina V. Palamarchuk, Ivan V. Kulakov & Alexander S. Fisyuk

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  1. Anton L. Shatsauskas
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  2. Anton A. Abramov
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  3. Elina R. Saibulina
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  4. Irina V. Palamarchuk
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  5. Ivan V. Kulakov
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  6. Alexander S. Fisyuk
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Correspondence to Alexander S. Fisyuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(2), 186–191

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Shatsauskas, A.L., Abramov, A.A., Saibulina, E.R. et al. Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives. Chem Heterocycl Comp 53, 186–191 (2017). https://doi.org/10.1007/s10593-017-2038-4

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  • DOI: https://doi.org/10.1007/s10593-017-2038-4

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