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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Notes

  1. The signal for the 1-NH proton was not observed, probably because of deuterium exchange.

References

  1. R. C. A. Isaacs, K. J. Cutrona, C. L. Newton, P. E. J. Sanderson, M. G. Solinsky, E. P. Baskin, I-W. Chen, C. M. Cooper, J. J. Cook, S. J. Gardell, S. D. Lewis, R. J. Lucas, Jr., E. A. Lyle, J. J. Lynch, Jr., A. M. Naylor-Olsen, M. T. Stranieri, K. Vastag, and J. P. Vacca, Bioorg. Med. Chem. Lett., 8, 1719 (1998).

  2. P. K. Gupta, P. A. McKernau, G. R. Revankar, A. D. Cook, R. K. Robins, N. K. Dalby, P. C. Canonico, and A. D. Adams, J. Med. Chem., 27, 1389 (1984).

    Article  Google Scholar 

  3. W. S. Saari, J. S. Wai, T. E. Fisher, C. M. Thomas, J. M. Hoffman, C. S. Rooney, A. M. Smith, J. H. Jones, D. L. Bamberger, M. E. Goldman, J. A. O'Brien, J. H. Nunberg, J. C. Quintero, W. A. Schleif, E. A. Emini, and P. S. Anderson, J. Med. Chem., 21, 3792 (1992).

    Article  Google Scholar 

  4. A. Ward, R. N. Brogden, R. C. Heel, T. M. Speight, and G. S. Avery, Drugs, 26, 468 (1983).

    Article  CAS  Google Scholar 

  5. P. S. Dragovich, T. J. Prins, R. Zhou, E. L. Brown, F. C. Maldonado, S. A. Fuhrman, L. S. Zalman, T. Tuntland, C. A. Lee, A. K. Patick, D. A. Matthews, T. F. Hendrickson, M. B. Kosa, B. Liu, M. R. Batugo, J. P. R. Gleeson, S. K. Sakata, L. Chen, M. C. Guzman, J. W. Meador, R. A. Ferre, and S. T. Worland, J. Med. Chem., 45, 1607 (2002).

    Article  CAS  Google Scholar 

  6. A. Le Tiran, J. P. Stables, and H. Kohn, Bioorg. Med. Chem., 9, 2693 (2001).

    Article  Google Scholar 

  7. L. Somsák, L. Kovács, M. Tóth, E. Osz, L. Szilágyi, Z. Györgydeák, Z. Dinya, T. Docsa, B. Tóth, and P. Gergely, J. Med. Chem., 44, 2843 (2001).

    Article  Google Scholar 

  8. H.-G. Lerchen, J. Baumgarten, K. von dem Bruch, T. E. Lehmann, M. Sperzel, G. Kempka, and H.-H. Fiebig, J. Med. Chem., 44, 4186 (2001).

    Article  CAS  Google Scholar 

  9. M. D. Mashkovskii, Drugs of the 20 th Century [in Russian], Novaya Volna, Moscow (1998), p. 320.

    Google Scholar 

  10. V. V. Mozolis and S. I. Iokubaitite, Usp. Khim., 7, 1310 (1973).

    Google Scholar 

  11. D. S. Goncharov, A. S. Kostyuchenko, and A. S. Fisyuk, Khim. Geterotsikl. Soedin., 1005 (2009). [Chem. Heterocycl. Compd., 45, 793 (2009)].

    Article  CAS  Google Scholar 

  12. A. S. Fisyuk, I. V. Kulakov, D. S. Goncharov, O. S. Nikitina, Yu. P. Bogza, and A. L. Shatsauskas, Khim. Geterotsikl. Soedin., 241 (2014). [Chem. Heterocycl. Compd., 50, 217 (2014)].

    Article  CAS  Google Scholar 

  13. V. P. Kislyi, A. M. Shestopalov, N. D. Kagramanov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 559 (1997). [Russ. Chem. Bull., 46, 539 (1997)].

    Article  CAS  Google Scholar 

  14. I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, B. T. Ibragimov, S. A. Talipov, Z. M. Zhambekov, A. A. Ainabaev, and K. M. Turdybekov, Khim. Prirod. Soedin., 183 (2009). [Chem. Nat. Compd., 45, 209 (2009)].

    Article  CAS  Google Scholar 

  15. I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, A. A. Ainabaev, K. M. Turdybekov, and A. M. Gazaliev, Khim. Prirod. Soedin., 56 (2009). [Chem. Nat. Compd., 45, 66 (2009)].

    Article  CAS  Google Scholar 

  16. I. V. Kulakov, D. M. Turdybekov, O. A. Nurkenov, G. M. Isabaeva, A. S. Makhmutova, K. M. Turdybekov, and S. D. Fazylov, Khim. Geterotsikl. Soedin., 1395 (2009). [Chem. Heterocycl. Compd., 45, 1117 (2009)].

    Article  CAS  Google Scholar 

  17. I. V. Kulakov and D. M. Turdybekov, Khim. Prirod. Soedin., 494 (2010). [Chem. Nat. Compd., 46, 586 (2010)].

    Article  CAS  Google Scholar 

  18. S. E. Tkachenko, A. N. Pushin, V. B. Sokolov, V. M. Fedoseev, and I. V. Martynov, Khim. Geterotsikl. Soedin., 381 (1998). [Chem. Heterocycl. Compd., 34, 347 (1998)].

    Article  CAS  Google Scholar 

  19. I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, and K. M. Turdybekov, Khim. Prirod. Soedin., 216 (2010). [Chem. Nat. Compd., 46, 257 (2010)].

    Article  CAS  Google Scholar 

  20. N. J. Miller, C. Rice-Evans, M. J. Davies, V. Gopinathan, and A. Milner, Clin. Sci., 84, 407 (1993).

    CAS  Google Scholar 

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

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Authors and Affiliations

  1. F. M. Dostoevskii State University, 55a Mir Ave., Omsk, 644077, Russia

    I. V. Kulakov, O. S. Nikitina, A. S. Fisyuk & D. S. Goncharov

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

    A. S. Fisyuk

  3. Nazarbayev University, Center for Life Sciences, 53 Kabanbai Batyr Ave., Astana, 010000, Kazakhstan

    Z. T. Shul’gau & A. E. Gulyaev

Authors
  1. I. V. Kulakov
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  2. O. S. Nikitina
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  3. A. S. Fisyuk
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  4. D. S. Goncharov
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  5. Z. T. Shul’gau
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  6. A. E. Gulyaev
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Correspondence to I. V. Kulakov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 729-736, May, 2014.

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Kulakov, I.V., Nikitina, O.S., Fisyuk, A.S. et al. Synthesis and Intramolecular Cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea. Chem Heterocycl Comp 50, 670–676 (2014). https://doi.org/10.1007/s10593-014-1519-y

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  • DOI: https://doi.org/10.1007/s10593-014-1519-y

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