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.
Similar content being viewed by others
Notes
The signal for the 1-NH proton was not observed, probably because of deuterium exchange.
References
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).
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).
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).
A. Ward, R. N. Brogden, R. C. Heel, T. M. Speight, and G. S. Avery, Drugs, 26, 468 (1983).
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).
A. Le Tiran, J. P. Stables, and H. Kohn, Bioorg. Med. Chem., 9, 2693 (2001).
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).
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).
M. D. Mashkovskii, Drugs of the 20 th Century [in Russian], Novaya Volna, Moscow (1998), p. 320.
V. V. Mozolis and S. I. Iokubaitite, Usp. Khim., 7, 1310 (1973).
D. S. Goncharov, A. S. Kostyuchenko, and A. S. Fisyuk, Khim. Geterotsikl. Soedin., 1005 (2009). [Chem. Heterocycl. Compd., 45, 793 (2009)].
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)].
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)].
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)].
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)].
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)].
I. V. Kulakov and D. M. Turdybekov, Khim. Prirod. Soedin., 494 (2010). [Chem. Nat. Compd., 46, 586 (2010)].
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)].
I. V. Kulakov, O. A. Nurkenov, D. M. Turdybekov, and K. M. Turdybekov, Khim. Prirod. Soedin., 216 (2010). [Chem. Nat. Compd., 46, 257 (2010)].
N. J. Miller, C. Rice-Evans, M. J. Davies, V. Gopinathan, and A. Milner, Clin. Sci., 84, 407 (1993).
This work was carried out with the financial support of the Russian Foundation for Basic Research (project 11-03-00338a).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 729-736, May, 2014.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1519-y