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Synthesis and properties of 2-substituted 5-chloro-1,3-oxazole-4-carboxamides

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Abstract

Chlorination of 2-aryl-5-benzylsulfanyl-1,3-oxazole-4-carbonitrile in aqueous acetic acid at 50–60°C afforded new 2-aryl-5-chloro-1,3-oxazole-4-carboxamides. The reactivity of the chlorine atom with respect to the N-, O-, and S-nucleophiles was investigated.

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References

  1. Oxazoles: Synthesis, Reactions, and Spectroscopy, Palmer, D.C., Ed., Hoboken: John Wiley, 2003, Pt A, p. 255.

    Google Scholar 

  2. Moody, C.J. and Bagley, M.C., J. Chem. Soc., Perkin Trans. 1, 1998, no. 3, p. 601.

    Google Scholar 

  3. Jansen, R., Kunze, B., Reichenbach, H., Jurkiewicz, E., Hunsmann, G., and Hiifle, G., Lieb. Ann. Chem., 1992, no. 4, p. 357.

    Google Scholar 

  4. Morwick, T., Berry, A., Brickwood, J., Cardozo, M., Catron, K., De Turi, M., Emeigh, J., Homon, C., Hrapchak, M., Jacober, S., Jakes, S., Kaplita, P., Kelly, T.A., Ksiazek, J., Liuzzi, M., Magolda, R., Mao, C., Marshall, D., McNeil, D., Prokopowicz, A., Sarko, C., Scouten, E., Sledziona, C., Sun, S., Watrous, J., Wu, J.P., and Cywin, C.L., J. Med. Chem., 2006, vol. 49, no. 10, p. 2898.

    Article  CAS  Google Scholar 

  5. Katritch, V., Jaakola, V.-P., Lane, J.R., Lin, J., Izerman, A.P., Yeager, M., Kufareva, I., Stevens, R.C., and Abagyan, R., J. Med. Chem., 2010, vol. 53, no. 4, p. 1799.

    Article  CAS  Google Scholar 

  6. Reader, J.C., Ellard, J.M., Boffey, H., Taylor, S., Carr, A.D., Cherry, M., Wilson, M., and Owoare, R.B., Patent WO2008/139161, 2008.

  7. Badiger, S., Chebrolu, M., Frederiksen, M., Holzer, P., Hurth, K., Lueoend, R.M., Machauer, R., Moebitz, H., Neumann, U., Ra-mos, R., Rueeger, H., Tintelnot-Blomley, M., Veenstra, S.J., and Voegtle, M., US Patent 2011021520, 2011.

  8. Shablykin, O.V., Brovarets, V.S., and Drach, B.S., Russ. J. Gen. Chem., 2007, vol. 77, no. 5, p. 932.

    Article  CAS  Google Scholar 

  9. Pil’o, S.G., Prokopenko, V.M., Brovarets, V.S., and Drach, B.S., Russ. J. Gen. Chem., 2010, vol. 80, no. 7, p. 1345.

    Article  Google Scholar 

  10. Prokopenko, V.M., Pil’o, S.G., Vasilenko, A.N., and Brovarets, V.S., Russ. J. Gen. Chem., 2010, vol. 80, no. 11, p. 2358.

    Article  CAS  Google Scholar 

  11. Prokopenko, V.M., Pil’o, S.G., and Brovarets, V.S., Russ. J. Gen. Chem., 2011, vol. 81, no. 2, p. 405.

    Article  CAS  Google Scholar 

  12. Kornienko, A.N., Golovchenko, A.B., Osadchuk, T.V., and Brovarets, V.S., Russ. J. Gen. Chem., 2011, vol. 81, no. 7, p. 1402.

    Google Scholar 

  13. Kornienko, A.N., Pil’o, S.G., Prokopenko, V.M., and Brovarets, V.S., Russ. J. Gen. Chem., 2012, vol. 82, no. 11, p. 1855.

    Article  CAS  Google Scholar 

  14. Drach, B.S., Sviridov, E.P., and Lavrenyuk, T.Ya., Zh. Org. Khim., 1974, vol. 10, no. 6, p. 1271.

    CAS  Google Scholar 

  15. Cornforth, J.W., The Chemistry of Penicillin, Princeton: Princeton University Press, 1949, p. 722.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 1, Kyiv, 02660, Ukraine

    A. N. Kornienko, S. G. Pil’o, V. M. Prokopenko & V. S. Brovarets

Authors
  1. A. N. Kornienko
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  2. S. G. Pil’o
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  3. V. M. Prokopenko
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  4. V. S. Brovarets
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Corresponding author

Correspondence to V. S. Brovarets.

Additional information

Original Russian Text © A.N. Kornienko, S.G. Pil’o, V.M. Prokopenko, V.S. Brovarets, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 6, pp. 1007–1010

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Kornienko, A.N., Pil’o, S.G., Prokopenko, V.M. et al. Synthesis and properties of 2-substituted 5-chloro-1,3-oxazole-4-carboxamides. Russ J Gen Chem 84, 1186–1189 (2014). https://doi.org/10.1134/S1070363214060206

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  • DOI: https://doi.org/10.1134/S1070363214060206

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