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Polyfunctional Pyrazoles. 9*. Synthesis of 1-Alkyl(Aryl)-3-[4-(Hydroxymethyl)-1Н-Pyrazol-3-Yl]UReas

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Chemistry of Heterocyclic Compounds Aims and scope

We have developed an effective method for the preparation of 1-alkyl(aryl)-3-[4-(hydroxymethyl)-1Н-pyrazol-3-yl]ureas based on the interaction of 4-hydroxymethylpyrazole-3-carbonyl azides with primary aliphatic and aromatic amines under the conditions of Curtius reaction. In the absence of amines in the reaction mixture, in situ generated 4-hydroxymethyl-3-isocyanatopyrazoles underwent intramolecular cyclization to pyrazolo[3,4-d][1,3]oxazin-6(4Н)-ones. The latter showed a tendency to form 1-alkyl(aryl)-3-[4-(hydroxymethyl)-1Н-pyrazol-3-yl]ureas in the presence of amines.

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References

  1. M. K. Bratenko, M. M. Barus, and M. V. Vovk, Chem. Heterocycl. Compd., 49, 1345 (2013). [Khim. Geterotsikl. Soedin., 1443 (2013).]

    Article  CAS  Google Scholar 

  2. C. Jamieson, J. K. F. Maclean, C. I. Brown, R. A. Campbell, K. J. Gillen, J. Gillespie, B. Kazemier, M. Kiczun, Y. Lamont, A. J. Lyons, E. M. Moir, J. A. Morrow, J. Pantling, Z. Rankovic, and L. Smith, Bioorg. Med. Chem. Lett., 21, 805 (2011).

    Article  CAS  Google Scholar 

  3. M. Elkady, R. Nieß, A. M. Schaible, J. Bauer, S. Luderer, G. Ambrosi, O. Werz, and S. A. Laufer, J. Med. Chem., 55, 8958 (2012).

    Article  CAS  Google Scholar 

  4. W. K. Anderson and A. N. Jones, J. Med. Chem., 27, 1559 (1984).

    Article  CAS  Google Scholar 

  5. M.-P. Cherrier, E. Parmantier, H. Minoux, F. Clerc, O. Angouillant-Boniface, M. Brollo, and L. Schio, US Pat. Appl. 2009197866.

  6. M. Clare, T. R. Fletcher, B. C. Hamper, G. A. Hanson, R. F. Heier, H. Huang, P. J. Lennon, D. S. Oburn, M. T. Redding, M. A. Stealey, S. G. Woltson, and J. Xie, WO Pat. Appl. 2005037797.

  7. D. Nguyen, H. Kelly, K. Moffett, E. L. Michelotti, and B. Liu, US Pat. Appl. 20100041642.

  8. A. V. Anikin, V. P. Gantla, V. E. Gregor, L. Jiang, Y. Liu, D. P. C. McGee, C. C. Mikel, J. C. Pickens, T. R. Webb, Y. Zheng, T. Zhu, A. Kadushkin, S. Zozulya, A. Chucholowski, D. E. McGrath, and S. Sviridov, WO Pat. Appl. 2007056155.

  9. K. Hirota, H. Sajiki, Y. Isobe, Y. Ohba, H. Morita, H. Takaku, and N. Chiba, US Pat. Appl. 5849779.

  10. T. Nakajima, K. Ueno, Y. Nomoto, Y. Matsumoto, H. Yano, S. Nakanishi, K. Takasaki, and H. Kusaka, EP Pat. Appl. 1637532.

  11. M. K. Bratenko, M. M. Barus, and M. V. Vovk, Chem. Heterocycl. Compd., 48, 1545 (2013). [Khim. Geterotsikl. Soedin., 1657 (2012).]

    Article  CAS  Google Scholar 

  12. S. Bräse, C. Gil, K. Knepper, and V. Zimmermann, Angew. Chem., 44, 5188 (2005).

    Article  Google Scholar 

  13. R. Boulahjar, A. Ouach, C. Matteo, S. Bourg, M. Ravache, R. le Guével, S. Merionneau, T. Oullier, O. Lozach, L. Meijer, G. Guguen-Cuillouzo, S. Lazar, M. Akssira, Y. Troin, G. Guillaumet, and S. Routier, J. Med. Chem., 55, 9589 (2012).

    Article  CAS  Google Scholar 

  14. R. Neidlein and Z. Sui, Synthesis, 658 (1991).

  15. R. Bohm, Pharmazie, 45, 282 (1990).

    Google Scholar 

  16. G. N. Pershin (editor), Methods of Experimental Chemotherapy [in Russian], Meditsina, Moscow (1971).

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Authors and Affiliations

  1. Bukovinian State Medical University, 2 Teatral’na Sq., Chernivtsi, 58002, Ukraine

    M. K. Bratenko, M. M. Barus & D. V. Rotar

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02094, Ukraine

    M. V. Vovk

Authors
  1. M. K. Bratenko
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  2. M. M. Barus
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  3. D. V. Rotar
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  4. M. V. Vovk
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Correspondence to M. K. Bratenko.

Additional information

*For Communication 8, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1359-1365, September, 2014.

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Bratenko, M.K., Barus, M.M., Rotar, D.V. et al. Polyfunctional Pyrazoles. 9*. Synthesis of 1-Alkyl(Aryl)-3-[4-(Hydroxymethyl)-1Н-Pyrazol-3-Yl]UReas. Chem Heterocycl Comp 50, 1252–1258 (2014). https://doi.org/10.1007/s10593-014-1587-z

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  • DOI: https://doi.org/10.1007/s10593-014-1587-z

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