Advertisement

Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1531–1536 | Cite as

Reaction of Imidazoles and Triazoles with 1-(Benzotriazol-1-yl)-2-iodoethanone

  • L. V. Zhilitskaya
  • L. G. Shagun
  • I. A. Dorofeev
  • N. O. Yarosh
  • L. I. Larina
Article
  • 17 Downloads

Abstract

Reactions of 2-methyl-1H-imidazole, 1H-benzimidazole, 4H-1,2,4-triazole, and 1H-benzotriazole with 1-(1H-benzotriazol-1-yl)-2-iodoethan-1-one in the absence of a base gave the corresponding N-mono- and N,N′-disubstituted derivatives. 4H-1,2,4-Triazole-3-thiol reacted with 1-(1H-benzotriazol-1-yl)-2-iodoethan-1- one to afford 1-([1,3]thiazolo[2,3-c][1,2,4]triazol-5-yl)-1H-benzotriazolium triiodide.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Gowda, J., Khader, A.M.A., Kalluraya, B., Padma Shree, and Shabaraya, A.R., Eur. J. Med. Chem., 2011, vol. 46, p. 4100.CrossRefGoogle Scholar
  2. 2.
    Amir, M., Ahsan, I., Akhter, W., Khan, S.A., and Ali, I., Indian J. Chem., Sect. B, 2011, vol. 50, p. 207.Google Scholar
  3. 3.
    Sondhi, S.M., Rajvanshi, S., Johar, M., Bharti, N., Azam, A., and Singh, A.K., Eur. J. Med. Chem., 2002, vol. 37, p. 835.CrossRefGoogle Scholar
  4. 4.
    Khalifa, M.M. and Abdelbaky, N.A., Arch. Pharm. Res., 2008, vol. 31, p. 419.CrossRefGoogle Scholar
  5. 5.
    Umut, S.G., Nesrin, G.K., Ozgur, G., Yavuz, K., Ekrem, K., and Samil, I., Bioorg. Med. Chem., 2007, vol. 15, p. 5738.CrossRefGoogle Scholar
  6. 6.
    Dias, L.R. and Salvador, R.R.S., Pharmaceuticals, 2012, vol. 5, p. 317.CrossRefGoogle Scholar
  7. 7.
    Suresh Kumar, G.V., Rajendra Prasad, Y., Mallikarjuna, B.P., and Chandrashekar, S.M., Eur. J. Med. Chem., 2010, vol. 45, p. 5120.CrossRefGoogle Scholar
  8. 8.
    Palekar, V.S., Damle, A.J., and Shukla, S.R., Eur. J. Med. Chem., 2009, vol. 44, p. 5112.CrossRefGoogle Scholar
  9. 9.
    Atia, A.J.K., Molecules, 2009, vol. 14, p. 2431.CrossRefGoogle Scholar
  10. 10.
    Dawane, B.S., Konda, S.G., Mandawad, G.G., and Shaikh, B.M., Eur. J. Med. Chem., 2010, vol. 45, p. 387.CrossRefGoogle Scholar
  11. 11.
    Demirayak, S.E., Benklia, K., and Guven, K., Eur. J. Med. Chem., 2000, vol. 35, p. 1037.CrossRefGoogle Scholar
  12. 12.
    Bishnoi, A., Srivastava, K., and Tripathi, C.K.M., Indian J. Chem., Sect. B, 2006, vol. 45, p. 2136.Google Scholar
  13. 13.
    Roue, M., Domart-Coulon, I., Ereskovsky, A., Djediat, C., Perez, T., and Bourguet-Kondracki, M., J. Nat. Prod., 2010, vol. 73, p. 1277.CrossRefGoogle Scholar
  14. 14.
    Baldaniya, B.B., Eur. J. Chem., 2010, vol. 7, p. 81Google Scholar
  15. 15.
    Abdelhamid, A.O., Abdelall, E.K.A., Abdel-Riheem, N.A., and Ahmed, S.A., Phosphorus, Sulfur Silicon Relat. Elem., 2010, vol. 185, p. 709.CrossRefGoogle Scholar
  16. 16.
    Rani, N., Sharma, A., and Singh, R., Mini Rev. Med. Chem., 2013, vol. 13, p. 1812.CrossRefGoogle Scholar
  17. 17.
    Cetin, A. and Geçibesler, I.H., J. Appl. Pharm. Sci., 2015, vol. 5, p. 120.CrossRefGoogle Scholar
  18. 18.
    Ubale, P.N., Vartale, S.P., and Sontakke, S.G., Asian J. Res. Chem., 2017, vol. 10, p. 573.CrossRefGoogle Scholar
  19. 19.
    Crotty, S., Maag, D., Arnold, J.J., Zhong, W., Lau, J.Y.N., Hong, Z., Andino, R., and Cameron, C.E., Nature Med., 2000, vol. 6, p. 1375.CrossRefGoogle Scholar
  20. 20.
    Nunes, J.J., Zhu, X.T., Amouzegh, P., Ghiron, C., Johnston, D.N., and Power, E.C., WO patent no. 2005 009 443, 2005; Chem. Abstr., 2005, vol. 142, no. 198 088.Google Scholar
  21. 21.
    Prajapati, B.R., Seth, A.K., Molvi, A.K., Mansuri, M.M., and Desai, D.G., Int. J. Pharm. Sci., 2011, p. 1473.Google Scholar
  22. 22.
    Coombes, R.C., Wynne, C.H., and Dowsett, M., Endocr.-Relat. Cancer, 1999, vol. 6, p. 259.CrossRefGoogle Scholar
  23. 23.
    Shinohara, K., Bando, T., and Sugiyama, H., Anticancer Drugs, 2010, vol. 21, p. 228.CrossRefGoogle Scholar
  24. 24.
    Grimison, A., Ridd, J.H., and Smith, B., J. Chem. Soc., 1960, p. 1352.Google Scholar
  25. 25.
    Rhône-Pouleng, FR Patant no. 2 077 811, 1970; Chem. Abstr., 1972, vol. 77, no. 88 508 v.Google Scholar
  26. 26.
    Loozen, H.J.J., Drouen, J.J.M., and Piepers, O., J. Org. Chem., 1975, vol. 40, p. 3279.CrossRefGoogle Scholar
  27. 27.
    Kochergin, P.M., Mashkovskii, M.D., Druzhinina, A.A., and Kaminka, E., Pharm. Chem. J., 1976, vol. 10, p. 474.CrossRefGoogle Scholar
  28. 28.
    Diez-Barra, E., Hoz, A., Sanchez, A., and Tejeda, J., Synth. Commun., 1993, vol. 23, p. 1783.CrossRefGoogle Scholar
  29. 29.
    Casilda, V.C., Perez-Mayoral, E., Banares, M.A., and Diz, E.L., Chem. Eng. J., 2010, vol. 161, p. 371.CrossRefGoogle Scholar
  30. 30.
    Hay, M.P., Wilson, W.R., and Denny, W.A., Tetrahedron, 2000, vol. 56, p. 645.CrossRefGoogle Scholar
  31. 31.
    Rajakumar, P. and Murali, V., Tetrahedron, 2000, vol. 56, p. 7995.CrossRefGoogle Scholar
  32. 32.
    Meyer, D. and Strassner, T., J. Org. Chem., 2011, vol. 76, p. 305.CrossRefGoogle Scholar
  33. 33.
    Katritzky, A.R., Kuzmerkiewicz, W., and Greenhill, J., Recl. Trav. Chim. Pays-Bas, 1991, vol. 110, p. 369.CrossRefGoogle Scholar
  34. 34.
    Gromova, S.A., Barmin, M.I., Kolesnikova, O.A., Shlyapochnikov, V.A., and Mel’nikov, V.V., Russ. J. Org. Chem., 1996, vol. 32, p. 1190.Google Scholar
  35. 35.
    Abdel-Megid, M., Elnagdi, M.H., and Negm, A.M., J. Heterocycl. Chem., 2002, vol. 39, p. 105.CrossRefGoogle Scholar
  36. 36.
    Akkurt, M., Yalçin, S.P., Sireci, N., Küçükbay, H., and Tahir, M.N., Acta Crystallogr., Sect. E, 2010, vol. 66, p. 253.CrossRefGoogle Scholar
  37. 37.
    Kücükbay, H., Şireci, N., Yilmaz, Ü., Deniz, S., Akkurt, M., Baktir, Z., and Büyükgüngör, O., Turk. J. Chem., 2012, vol. 36, p. 201.Google Scholar
  38. 38.
    Grimmett, M.R., Imidazole and Benzimidazole Synthesis, Meth-Cohn, O. and Katritzky, A.R., Eds., New York: Academic, 1997, p. 201.Google Scholar
  39. 39.
    Barnum, C.S., Moberg, W.K., Olson, R.E., and Moberg, W.K., Eur. Patent no. 296 745, 1988; Chem. Abstr., 1989, vol. 110, no. 173 241 x.Google Scholar
  40. 40.
    Moreau, J.J.E., Vellutini, L., Man, M.W.C., Bied, C., Bantigniès, J.L., Dieudonné, P., and Sauvajol, J.L., J. Am. Chem. Soc., 2001, vol. 123, p. 7957.CrossRefGoogle Scholar
  41. 41.
    Kizhnyaev, V.N., Golobokova, T.V., Pokatilov, F.A., Vereshchagin, L.I., and Estrin, Ya.I., Chem. Heterocycl. Compd., 2017, vol. 53, no. 6/7, p. 682.Google Scholar
  42. 42.
    Katritzky, A.R. and Pastor, A., J. Org. Chem., 2000, vol. 65, p. 3679.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • L. V. Zhilitskaya
    • 1
  • L. G. Shagun
    • 1
  • I. A. Dorofeev
    • 1
  • N. O. Yarosh
    • 1
  • L. I. Larina
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

Personalised recommendations