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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 5, pp 670–676 | Cite as

Synthesis and Intramolecular Cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

  • I. V. KulakovEmail author
  • O. S. Nikitina
  • A. S. Fisyuk
  • D. S. Goncharov
  • Z. T. Shul’gau
  • A. E. Gulyaev
Article

The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.

Keywords

3-aminopyridin-2(1H)-ones isothiocyanates 1,3-thiazines 1,3-thiazolines thioureas intramolecular cyclization 

Notes

This work was carried out with the financial support of the Russian Foundation for Basic Research (project 11-03-00338a).

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • I. V. Kulakov
    • 1
    Email author
  • O. S. Nikitina
    • 1
  • A. S. Fisyuk
    • 1
    • 2
  • D. S. Goncharov
    • 1
  • Z. T. Shul’gau
    • 3
  • A. E. Gulyaev
    • 3
  1. 1.F. M. Dostoevskii State UniversityOmskRussia
  2. 2.Omsk State Technical UniversityOmskRussia
  3. 3.Nazarbayev University, Center for Life SciencesAstanaKazakhstan

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