The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1Н)-ones, substituted with a pyridine ring at position 3. The reactions of these compounds with hydrazine hydrate produced 3-aminopyridin-2(1Н)-ones. The synthesis of 1H-pyrido[2,3-b][1, 4]oxazin-2(3H)-ones was accomplished by a reaction of 3-aminopyridin-2(1Н)-ones with chloroacetyl chloride.
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This work received financial support from the Russian Foundation for Basic Research (project 11-03-00338-а) and the Ministry of Education and Science of the Russian Federation in the framework of the project 2596.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 241-249, February, 2014.
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Fisyuk, A.S., Kulakov, I.V., Goncharov, D.S. et al. Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones. Chem Heterocycl Comp 50, 217–224 (2014). https://doi.org/10.1007/s10593-014-1464-9
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DOI: https://doi.org/10.1007/s10593-014-1464-9