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Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides

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Chemistry of Heterocyclic Compounds Aims and scope

Under Curtius rearrangement conditions, 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides form the corresponding isocyanates which react in situ with ammonia, primary and secondary amines to form mono-, di-, and trisubstituted ureas. The reaction of the 5-ethoxycarbonyl-2,6-dimethylnicotinic acid azide with imidazole under these conditions gave symmetrical N,N'-bis[5-(ethoxycarbonyl)-2,6-di-methylpyridin-3-yl]ureas.

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References

  1. T. Honma, K. Hayashi, T. Aoyama, N, Hashimoto, T. Machida, K. Fukasawa, T. Iwama, Ch. Ikeura, M. Ikuta, I. Suzuki-Takahashi, Y. Iwasawa, T. Hayama, S. Nishimura, and H. Morishima, J. Med. Chem., 44, 4615 (2001).

    Article  CAS  Google Scholar 

  2. Ch.-H. Chien, M. Leung, J.-K. Su, G.-H. Li, Y.-H.Liu, and Y. Wang, J. Org. Chem., 69, 1866 (2004).

    Article  CAS  Google Scholar 

  3. N. Mibu, K. Yokomizo, T. Miyata, and K. Sumoto, Chem. Pharm. Bull., 55, 1406 (2007).

    Article  CAS  Google Scholar 

  4. W. Bolhofer, E. J. Cragoe, and J. M. Hoffman, US Pat. Appl. 4203988.

  5. G. J. Durant and C. R. Ganellin, US Pat. Appl. 4215125.

  6. S. T. Baibaeva, L. A. Mirkind, L. P. Krylova, E. A. Navyazhskaya, and A. S. Salova, Methods for the Analysis of Varnish-and-Paint Materials [in Russian], Khimiya, Moscow (1974), p. 182.

    Google Scholar 

  7. E. Yu. Nesterova, A. S. Pugacheva, and M. V. Voevudsky, Vopr. Khimiyi i Khim. Tekhnol., 2 , 13 (2009).

    Google Scholar 

  8. M. R. Pavia, S. J. Lobbestael, Ch. P. Taylor, F. M. Hershenson, and D. L. Miskell, J. Med. Chem., 33, 854 (1990).

    Article  CAS  Google Scholar 

  9. F. Otón, A. Tarraga, A. Espínosa, M. D. Velasco, and P. Molína, J. Org. Chem., 71, 4590 (2006).

    Article  Google Scholar 

  10. N. S. Vul’fson, V. G. Zaikin, and A. I. Mikaya, Mass Spectrometry of Organic Compounds [in Russian], Khimiya, Moscow (1986), p. 258, 263.

  11. A. N. Fedotov, E. V. Trofimova, V. A. Romanov, S. S. Mochalov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 115 (2008). [Chem. Heterocycl. Compd., 44, 96 (2008)].

  12. E. Yu. Nesterova, A. S. Pugacheva, M. V. Voevudsky, O. Yu. Glazyrina, and E. S. Kositsina, Vestn. DNU, issue 12, 86 (2006).

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Authors and Affiliations

  1. Oles’ Gonchar Dnepropetrovsk National University, 72 Gagarin Ave., Dnepropetrovsk, 49010, Ukraine

    E. Yu. Nesterova & A. S. Pugacheva

  2. Ukrainian State Chemical-technological University, 8 Gagarin Ave., Dnepropetrovsk, 49005, Ukraine

    M. V. Voevudsky

Authors
  1. E. Yu. Nesterova
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  2. A. S. Pugacheva
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  3. M. V. Voevudsky
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Correspondence to M. V. Voevudsky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1272-1281, August, 2012.

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Nesterova, E.Y., Pugacheva, A.S. & Voevudsky, M.V. Substituted ureas based on 2,6-dimethyl-3,5-pyridinedicarboxylic acid azides. Chem Heterocycl Comp 48, 1187–1195 (2012). https://doi.org/10.1007/s10593-012-1120-1

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  • DOI: https://doi.org/10.1007/s10593-012-1120-1

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