Chemistry of Heterocyclic Compounds

, Volume 50, Issue 2, pp 217–224 | Cite as

Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones

  • A. S. Fisyuk
  • I. V. Kulakov
  • D. S. Goncharov
  • O. S. Nikitina
  • Y. P. Bogza
  • A. L. Shatsauskas

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.


3-aminopyridin-2(1Н)-ones Enamino ketones N-(3-oxoalkenyl)amides Chloroacetamides Intramolecular cyclization 


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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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • A. S. Fisyuk
    • 1
    • 2
  • I. V. Kulakov
    • 1
  • D. S. Goncharov
    • 1
  • O. S. Nikitina
    • 1
  • Y. P. Bogza
    • 1
  • A. L. Shatsauskas
    • 1
  1. 1.Omsk F. M. Dostoevsky State UniversityOmskRussia
  2. 2.Omsk State Technical UniversityOmskRussia

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