Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 2, pp 204–211 | Cite as

Catalytic Aminomethylation of Aminobenzamides with Bis(N,N-dimethylamino)methane and Carbamides

  • R. R. KhairullinaEmail author
  • T. V. Tyumkina
  • A. R. Geniyatova
  • F. K. Mullagil’dina
  • A. G. Ibragimov
Article

Abstract

An effective method was developed for the synthesis of acyclic aniline derivatives bearing carbamide fragments by the reaction of carbamides with ortho-, meta-, and para-aminobenzamides and bis(N,N-dimethylamino) methane in the presence of NiCl2·6H2O and SmCl3·6H2O as catalysts.

Keywords

aminomethylation aminobenzamides bis(N,N-dimethylamino)methane carbamides 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    El-Shamy, I.E., Abdel-Mohsen, A.M., Alsheikh, A.A., Fouda, M.M.G., Al-Deyab, S.S., El-Hashash, M.A., and Jancar, J., Dyes and Pigments, 2015, vol. 113, p. 357. doi 10.1016/j.dyepig.2014.08.026CrossRefGoogle Scholar
  2. 2.
    Bogdanov, A.V., Vazykhova, A.M., Khasiyatullina, N.R., Krivolapov, D.B., Dobrynin, A.B., Voloshina, A.D., and Mironov, V.F., Chem. Heterocycl. Compd., 2016, vol. 52, no. 1, p. 25. doi 10.1007/s10593-016-1826-6CrossRefGoogle Scholar
  3. 3.
    Ertan, M., Tayhan, A.B., and Yulug, N., Arch. Pharm., 1990, vol. 323, p. 605. doi 10.1002ardp.19903230910CrossRefGoogle Scholar
  4. 4.
    Gazieva, G.A., Lozhkin, P.V., and Kravchenko, A.N., Chem. Heterocycl. Compd., 2007, vol. 43, no. 11, p. 1406. doi 10.1007/s10593-007-0217-4CrossRefGoogle Scholar
  5. 5.
    Shen, X.X., Shen, Yi.L., Han, Yi.F., and Liu, Qi., Adv. Mater. Res., 2012, vol. 441, p. 421. doi 10.4028/www.scientific.net/AMR.441.421CrossRefGoogle Scholar
  6. 6.
    Maleki, B. and Baghayeri, M., RSC Adv., 2015, vol. 97, no. 5, p. 79746. doi 10.1039C5RA16481HCrossRefGoogle Scholar
  7. 7.
    Petersen, H., Synthesis, 1973, vol. 5, p. 243. doi 10.1055/s-1973-22190CrossRefGoogle Scholar
  8. 8.
    Paquin, A.M., Angew. Chem., 1948, vol. 60, p. 267.Google Scholar
  9. 9.
    Garibov, E.N., Rzaeva, I.A., Shykhaliev, N.G., Kuliev, A.I., Farzaliev, V.M., and Allakhverdiev, M.A., Russ. J. Appl. Chem., 2010, vol. 83, no. 4, p. 707. doi 10.1134/S1070427210040245CrossRefGoogle Scholar
  10. 10.
    Burke, W.J., J. Am. Chem. Soc., 1947, vol. 69, no. 9, p. 2136. doi 10.1021/ja01201a024CrossRefGoogle Scholar
  11. 11.
    Khairullina, R.R., Geniyatova, A.R., Ibragimov, A.G., and Dzemilev, U.M., Russ. J. Org. Chem., 2013, vol. 49, no. 6, p. 904. doi 10.1134/S1070428013060171CrossRefGoogle Scholar
  12. 12.
    Hairullina, R.R., Geniyatova, A.R., Ibragimov, A.G., and Dzemilev, U.M., Chem. Heterocycl. Compd., 2014, vol. 50, no. 5, p. 715. doi 10.1007/s10593-014-1525-0CrossRefGoogle Scholar
  13. 13.
    Walter, A.M. and Heilmayer, L., Antibiotika Fibel, Stuttgart: Thieme Verlag, 1965. S. 419.Google Scholar
  14. 14.
    Movassaghi, M., Siegel, D.S., and Han, S., Chem. Sci., 2010, no. 1, p. 561. doi 10.1039/C0SC00351DCrossRefGoogle Scholar
  15. 15.
    Ambrosio, M.D., Guerriero, A., Debitus, C., Ribes, O., Pusset, J., Leroy, S., and Pietra, F., J. Chem. Soc. Chem. Commun., 1993, p. 1305. doi 10.1039/C39930001305Google Scholar
  16. 16.
    Gorbatova, O.N., Zherbev, A.V., and Koroleva, O.V., Usp. Biol. Nauk., 2006, vol. 46, p. 323.Google Scholar
  17. 17.
    Farzaliev, V.M., Allakhverdiev, M.A., Magerramov, A.M., Shirinova, N.A., Dzavadova, L.A., Rzaeva, I.A., Khalilova, A.Z., and Aliev, F.Y., Russ. J. Appl. Chem., 2001, vol. 74, no. 1, p. 114. doi 10.1023/A:1012764404658CrossRefGoogle Scholar
  18. 18.
    McKerrecher, D., Allen, J.V., Caulkett, P.W.R., Donald, C.S., Fenwick, M.L., Grange, E., Johnson, K.M., Johnstone, C., Jones, C.D., Pike, K.G., Rayner, J.W., and Walker, R.P., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 2705. doi 10.1016/j.bmcl.2006.02.022CrossRefGoogle Scholar
  19. 19.
    Nishimura, T., Iino, T., Mitsuya, M., Bamba, M., Watanabe, H., Tsukahara, D., Kamata, K., Sasaki, K., Ohyama, S., Hosaka, H., Futamura, M., Nagata, Y., and Eiki Junichi, Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 1357. doi 10.1016/j.bmcl.2009.01.053CrossRefGoogle Scholar
  20. 20.
    More, P., Patil, A., and Salunkhe, R., RSC Adv., 2014, vol. 96, no. 4, p. 63039. doi 10.1039/c4ra09514fCrossRefGoogle Scholar
  21. 21.
    Kiyokawa, Sh., Hirata, Y., Nagaoka, Y., Shibano, M., Taniguchi, M., Yasuda, M., Baba, K., and Uesato, Sh., Bioorg. Med. Chem., 2010, vol. 18, p. 3925. doi 10.1016/j.bmc.2010.04.033CrossRefGoogle Scholar
  22. 22.
    Cai, J., Wei, H., Hong, K.H., Wu, X., Cao, M., Zong, X., Li, L., Sun, C., Chen, J., and Ji, M., Eur. J. Med. Chem., 2015, vol. 96, p. 1. doi 10.1016/j.ejmech.2015.04.002CrossRefGoogle Scholar
  23. 23.
    Caldini, R., Fanti, E., Magnelli, L., Barletta, E., Tanganelli, E., Zampieri, M., and Chevanne, M., Vascular Cell, 2011, vol. 3, p. 12. doi 10.1186/2045-824X-3-12CrossRefGoogle Scholar
  24. 24.
    Mabkhot, Y.N., Al-Majid, A.M., Barakat, A., Al-Showiman, S.S., Al-Har, M.S., Radi, S., Naseer, M.M., and Hadda, T.B., Int. J. Mol. Sci., 2014, vol. 15, p. 1503. doi 10.3390/ijms15035115CrossRefGoogle Scholar
  25. 25.
    Ailan, J.R., McCloy, B., Paton, A.D., Smith, W.E., and Gerrard, D.L., Thermochim. Acta, 1992, vol. 205, p. 127. doi 10.1016/0040-6031(92)85254-SCrossRefGoogle Scholar
  26. 26.
    Tramontini, M. and Angiolini, L., Tetrahedron, 1990, vol. 46, p. 1791. doi 10.1016/S0040-4020(01)89752-0CrossRefGoogle Scholar
  27. 27.
    Tramontini, M., Synthesis, 1973, no. 12, p. 703. doi 10.1055/s-1973-22294CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • R. R. Khairullina
    • 1
    Email author
  • T. V. Tyumkina
    • 1
  • A. R. Geniyatova
    • 1
  • F. K. Mullagil’dina
    • 1
  • A. G. Ibragimov
    • 1
  1. 1.Institute of Petrochemistry and Catalysis of the Russian Academy of SciencesUfaRussia

Personalised recommendations