Skip to main content
SpringerLink
Log in

4-substituted 2-chloromethyl[1,2,4]triazolo[1,5-a]benzimidazoles and their transformations

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

Abstract

2,4-Dimethyl[1,2,4]triazolo[1,5-a]benzimidazole reacted with bromine to give 7-bromo derivative through the corresponding stable perbromide. Cyclization of quaternary 1,2-diamino-3-R-benzimidazolium salts with chloroacetyl chloride in boiling xylene afforded 2-chloromethyl-4-R-[1,2,4]triazolo[1,5-a]benzimidazoles [R = Me, ArOCH2CH2, ArC(O)CH2] which readily underwent exchange reactions with nitrogen-, oxygen-, and sulfur-centered nucleophiles and Wittig reaction with formation of 2-vinyl derivatives.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Spasov, A.A., Chernikov, M.V., Anisimova, V.A., Kuz’menko, T.A., and Osipova, M.M., Pharm. Chem. J., 2000, vol. 34, no. 2, p. 48.

    Article  CAS  Google Scholar 

  2. De Graaf, Ch., Kooistra, A.J., Vischer, H.F., Katritch, V., Kuijer, M., Shiroishi, M., Iwata, S., Shimamura, T., Stevens, R.C., de Esch, I.J.P., and Leurs, R., J. Med. Chem., 2011, vol. 54, p. 8195.

    Article  Google Scholar 

  3. Kovalev, G.V., Kuz’menko, T.A., Kuz’menko, V.V., Spasov, A.A., Anisimova, V.A., and Simonov, A.M., USSR Inventor’s Certificate no. 1 427 787, 1988; Byull. Izobret., 2014, no. 18.

    Google Scholar 

  4. Kuz’menko, T.A., Kuz’menko, V.V., Kovalev, G.V., Spasov, A.A., and Dudchenko, G.P., USSR Inventor’s Certificate no. 1 438 179, 1988; Byull. Izobret., 2014, no. 18.

    Google Scholar 

  5. Korkhov, V.V., Makusheva, V.P., Kuz’menko, T.A., and Kuz’menko, V.V., USSR Inventor’s Certificate no. 1 640 981, 1990; Byull. Izobret., 2014, no. 18.

    Google Scholar 

  6. Silva-Santisteban, M.C., Westwood, I.M., Boxall, K., Brown, N., Peacock, S., McAndrew, C., Barrie, E., Richards, M., Mirza, A., Oliver, A.W., Burke, R., Hoelder, S., Jones, K., Aherne, G.W., Blagg, J., Collins, I., Garrett, M.D., and van Montfort, R.L.M., PLOS ONE, 2013, vol. 8, no. 6, p. e65689.

    Article  CAS  Google Scholar 

  7. Mohamed, B.G., Hussein, M.A., Abdel-Alim, A.-A.M., and Hashem, M., Arch. Pharm. Res., 2006, vol. 29, p. 26.

    Article  CAS  Google Scholar 

  8. Mohamed, B.G., Abdel-Alim, A.-A.M., and Hussein, M.A., Acta Pharm., 2006, vol. 56, p. 31.

    CAS  Google Scholar 

  9. Mohammed, A.F., Hussein, M.A., Abdel-Moty, S.G., and Abdel-Alim, A.-A.M., Bull. Pharm. Sci., Assiut Univ., 2011, vol. 34, no. 1, p. 77.

    Article  CAS  Google Scholar 

  10. Mahmoud, A.M., Salem, Ola I.A., Abdel Moty, S.G., and Abdel Alim, A.M., Indian J Pharm. Sci., 2013, vol. 75, p. 545.

    CAS  Google Scholar 

  11. Mohammed, A.F., Abdel-Moty, S.G., Hussein, M.A., and Abdel-Alim, A.-A.M., Arch. Pharm. Res., 2013, vol. 36, p. 1465.

    Article  CAS  Google Scholar 

  12. Kuz’menko, V.V., Kuz’menko, T.A., Pozharskii, A.F., Doronkin, V.N., Chikina, N.L., and Pozharskaya, S.S., Chem. Heterocycl. Compd., 1989, vol. 25, p. 168.

    Article  Google Scholar 

  13. Kuz’menko, T.A., Kuz’menko, V.V., Divaeva, L.N., Morkovnik, A.S., and Borodkin, G.S., Russ. Chem. Bull., Int. Ed., 2012, vol. 61, p. 1161.

    Article  Google Scholar 

  14. Kuz’menko, T.A., Kuz’menko, V.V, Morkovnik, A.S., and Divaeva, L.N., Chem. Heterocycl. Compd., 2006, vol. 42, p. 648.

    Article  Google Scholar 

  15. Sechin, S.R., Schetinger, M.R.C., Zanatta, N., Madruga, C.C., Hacholski, I.L., Flores, D.C., Banacorso, H.G., Martins, M.A.P., and Morsch, V.M., Chem. Res. Toxicol., 2003, vol. 16, p. 1433.

    Article  Google Scholar 

  16. Cosimelli, B., Greco, G., Ehlardo, M., Novellino, I., Da Settimo, F., Taliani, S., La Motta, C., Bellandi, M., Tuccinardi, T., Martinelli, A., Ciampi, O., Trincavelli, M.L., and Martini, C., J. Med. Chem., 2008, vol. 51, p. 1764.

    Article  CAS  Google Scholar 

  17. D’Angelo, N.D., Kim, T.-S., Andrews, K., Booker, S.K., Caenepeel, S., Chen, K., D’Amico, D., Freeman, D., Jiang, J., Liu, L., McCarter, J.D., San Miguel, T., Mullady, E.L., Schrag, M., Subramanian, R., Tang, J., Wahl, R.C., Wang, L., Whittington, D.A., Wu, T., Xi, N., Xu, Y., Yakowec, P., Yang, K., Zalameda, L.P., Zhang, N., Hughes, P., and Norman, M.H., J. Med. Chem., 2011, vol. 54, p. 1789.

    Article  Google Scholar 

  18. Mai, A., Sbardella, G., Artico, M., Ragno, R., Massa, S., Novellino, E., Greco, G., Lavecchia, A., Musiu, C., La Colla, M., Murgioni, C., La Colla, P., and Loddo, R., J. Med. Chem., 2001, vol. 44, p. 2544.

    Article  CAS  Google Scholar 

  19. Laufer, S.A. and Wagner, G.K., J. Med. Chem., 2002, vol. 45, p. 2733.

    Article  CAS  Google Scholar 

  20. Parent, A.A., Gunther, J.R., and Katzenellenbogen, J.A., J. Med. Chem., 2008, vol. 51, p. 6512.

    Article  CAS  Google Scholar 

  21. Hieke, M., Greiner, C., Dittrich, M., Reisen, F., Schneider, G., Schubert-Zsilavecz, M., and Werz, O., J. Med. Chem., 2011, vol. 41, p. 4490.

    Article  Google Scholar 

  22. Krapivin, G.D., Usova, E.B., Zavodnik, V.E., and Kul’nevich, V.G., Chem. Heterocycl. Compd., 1992, vol. 28, p. 890.

    Article  Google Scholar 

  23. Gel’man, N.E., Terent’eva, E.A., Shanina, T.M., and Kiparenko, L.M., Metody kolichestvennogo organicheskogo elementnogo analiza (Methods of Quantitative Organic Elemental Analysis), Moscow: Khimiya, 1987.

    Google Scholar 

  24. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Wallingford CT: Gaussian, 2004.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    T. A. Kuz’menko, L. N. Divaeva & A. S. Morkovnik

Authors
  1. T. A. Kuz’menko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. N. Divaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Morkovnik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Morkovnik.

Additional information

Original Russian Text © T.A. Kuz’menko, L.N. Divaeva, A.S. Morkovnik, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 10, pp. 1504–1509.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kuz’menko, T.A., Divaeva, L.N. & Morkovnik, A.S. 4-substituted 2-chloromethyl[1,2,4]triazolo[1,5-a]benzimidazoles and their transformations. Russ J Org Chem 51, 1474–1480 (2015). https://doi.org/10.1134/S1070428015100218

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015100218

Keywords

Search

Navigation