Skip to main content
Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Gowda, J., Khader, A.M.A., Kalluraya, B., Padma Shree, and Shabaraya, A.R., Eur. J. Med. Chem., 2011, vol. 46, p. 4100.

    Article  CAS  PubMed  Google Scholar 

  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. Sondhi, S.M., Rajvanshi, S., Johar, M., Bharti, N., Azam, A., and Singh, A.K., Eur. J. Med. Chem., 2002, vol. 37, p. 835.

    Article  CAS  PubMed  Google Scholar 

  4. Khalifa, M.M. and Abdelbaky, N.A., Arch. Pharm. Res., 2008, vol. 31, p. 419.

    Article  CAS  PubMed  Google Scholar 

  5. Umut, S.G., Nesrin, G.K., Ozgur, G., Yavuz, K., Ekrem, K., and Samil, I., Bioorg. Med. Chem., 2007, vol. 15, p. 5738.

    Article  CAS  Google Scholar 

  6. Dias, L.R. and Salvador, R.R.S., Pharmaceuticals, 2012, vol. 5, p. 317.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Suresh Kumar, G.V., Rajendra Prasad, Y., Mallikarjuna, B.P., and Chandrashekar, S.M., Eur. J. Med. Chem., 2010, vol. 45, p. 5120.

    Article  CAS  PubMed  Google Scholar 

  8. Palekar, V.S., Damle, A.J., and Shukla, S.R., Eur. J. Med. Chem., 2009, vol. 44, p. 5112.

    Article  CAS  PubMed  Google Scholar 

  9. Atia, A.J.K., Molecules, 2009, vol. 14, p. 2431.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Dawane, B.S., Konda, S.G., Mandawad, G.G., and Shaikh, B.M., Eur. J. Med. Chem., 2010, vol. 45, p. 387.

    Article  CAS  PubMed  Google Scholar 

  11. Demirayak, S.E., Benklia, K., and Guven, K., Eur. J. Med. Chem., 2000, vol. 35, p. 1037.

    Article  CAS  PubMed  Google Scholar 

  12. Bishnoi, A., Srivastava, K., and Tripathi, C.K.M., Indian J. Chem., Sect. B, 2006, vol. 45, p. 2136.

    Google Scholar 

  13. Roue, M., Domart-Coulon, I., Ereskovsky, A., Djediat, C., Perez, T., and Bourguet-Kondracki, M., J. Nat. Prod., 2010, vol. 73, p. 1277.

    Article  CAS  PubMed  Google Scholar 

  14. Baldaniya, B.B., Eur. J. Chem., 2010, vol. 7, p. 81

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  16. Rani, N., Sharma, A., and Singh, R., Mini Rev. Med. Chem., 2013, vol. 13, p. 1812.

    Article  CAS  PubMed  Google Scholar 

  17. Cetin, A. and Geçibesler, I.H., J. Appl. Pharm. Sci., 2015, vol. 5, p. 120.

    Article  CAS  Google Scholar 

  18. Ubale, P.N., Vartale, S.P., and Sontakke, S.G., Asian J. Res. Chem., 2017, vol. 10, p. 573.

    Article  Google Scholar 

  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.

    Article  CAS  PubMed  Google Scholar 

  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. 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. Coombes, R.C., Wynne, C.H., and Dowsett, M., Endocr.-Relat. Cancer, 1999, vol. 6, p. 259.

    Article  CAS  PubMed  Google Scholar 

  23. Shinohara, K., Bando, T., and Sugiyama, H., Anticancer Drugs, 2010, vol. 21, p. 228.

    Article  CAS  PubMed  Google Scholar 

  24. Grimison, A., Ridd, J.H., and Smith, B., J. Chem. Soc., 1960, p. 1352.

    Google Scholar 

  25. Rhône-Pouleng, FR Patant no. 2 077 811, 1970; Chem. Abstr., 1972, vol. 77, no. 88 508 v.

    Google Scholar 

  26. Loozen, H.J.J., Drouen, J.J.M., and Piepers, O., J. Org. Chem., 1975, vol. 40, p. 3279.

    Article  CAS  Google Scholar 

  27. Kochergin, P.M., Mashkovskii, M.D., Druzhinina, A.A., and Kaminka, E., Pharm. Chem. J., 1976, vol. 10, p. 474.

    Article  Google Scholar 

  28. Diez-Barra, E., Hoz, A., Sanchez, A., and Tejeda, J., Synth. Commun., 1993, vol. 23, p. 1783.

    Article  CAS  Google Scholar 

  29. Casilda, V.C., Perez-Mayoral, E., Banares, M.A., and Diz, E.L., Chem. Eng. J., 2010, vol. 161, p. 371.

    Article  CAS  Google Scholar 

  30. Hay, M.P., Wilson, W.R., and Denny, W.A., Tetrahedron, 2000, vol. 56, p. 645.

    Article  CAS  Google Scholar 

  31. Rajakumar, P. and Murali, V., Tetrahedron, 2000, vol. 56, p. 7995.

    Article  CAS  Google Scholar 

  32. Meyer, D. and Strassner, T., J. Org. Chem., 2011, vol. 76, p. 305.

    Article  CAS  PubMed  Google Scholar 

  33. Katritzky, A.R., Kuzmerkiewicz, W., and Greenhill, J., Recl. Trav. Chim. Pays-Bas, 1991, vol. 110, p. 369.

    Article  CAS  Google Scholar 

  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. Abdel-Megid, M., Elnagdi, M.H., and Negm, A.M., J. Heterocycl. Chem., 2002, vol. 39, p. 105.

    Article  CAS  Google Scholar 

  36. Akkurt, M., Yalçin, S.P., Sireci, N., Küçükbay, H., and Tahir, M.N., Acta Crystallogr., Sect. E, 2010, vol. 66, p. 253.

    Article  CAS  Google Scholar 

  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. Grimmett, M.R., Imidazole and Benzimidazole Synthesis, Meth-Cohn, O. and Katritzky, A.R., Eds., New York: Academic, 1997, p. 201.

    Google Scholar 

  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. 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.

    Article  CAS  PubMed  Google Scholar 

  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. Katritzky, A.R. and Pastor, A., J. Org. Chem., 2000, vol. 65, p. 3679.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. V. Zhilitskaya.

Additional information

Original Russian Text © L.V. Zhilitskaya, L.G. Shagun, I.A. Dorofeev, N.O. Yarosh, L.I. Larina, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 10, pp. 1519–1524.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhilitskaya, L.V., Shagun, L.G., Dorofeev, I.A. et al. Reaction of Imidazoles and Triazoles with 1-(Benzotriazol-1-yl)-2-iodoethanone. Russ J Org Chem 54, 1531–1536 (2018). https://doi.org/10.1134/S1070428018100159

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018100159

Navigation