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Russian Journal of General Chemistry

, Volume 89, Issue 8, pp 1570–1574 | Cite as

Synthesis of 2,3-Dihydro-1H-imidazo[1,2-a]pyridinium Systems by Halocyclization of 1-Alkenyl(propargyl)-2-aminopyridinium Halides

  • E. V. KalitaEmail author
  • D. G. Kim
  • D. A. Rakhmatullina
  • M. A. Pylneva
  • E. M. Krynina
Article
  • 6 Downloads

Abstract

Reaction of 2-aminopyridine with allyl bromide, methallyl chloride, 2-bromoallyl bromide, and propargyl bromide in acetone furnished 2-amino-1-allyl-, methallyl-, (2-bromoallyl)-, and propargylpyridinium halides. 2-Amino-1-allyl(methallyl)pyridinium halides reacted with bromine and iodine to form 2-halomethyl-2,3-dihydro-1H-imidazo[1,2-a]pyridinium systems. 2-Amino-1-(2-bromoallyl)pyridinium bromide underwent heterocyclization under the action of bromine, and did not react with iodine. 2-Amino-1-propargylpyridinium bromide reacted with bromine and iodine to form 2-halomemylene-2,3-dihydro-1H-imidazo[1,2-a]pyridinium systems.

Keywords

2-aminopyridine 2-amino-1-alkenyl(propargyl)pyridinium halide halocyclization 2,3-dihydro-1H-imidazo[1,2-a]pyridinium halide 

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Notes

Funding

This work was financially supported by the Government of the Russian Federation (Decree no. 211 of March 16, 2013, agreement no. 02.A03.21.0011) and the Ministry of Education and Science of the Russian Federation (project no. 4.9665.2017/8.9).

References

  1. 1.
    Marinescu, M., Int. J. Pharm. and Bio Sci., 2017, vol. 8, no. 2, p. 338. doi  https://doi.org/10.22376/ijpbs.2017.8.2.p338-355 CrossRefGoogle Scholar
  2. 2.
    Cai, Z.W., Wei, D., Schroeder, G.M., Cornelius, L.A.M., Kim, K., Chen, X.T., Schmidt, R.J. Williams, D.K., Tokarski, J.S., An, Y., Sack, J.S., Manne, V., Kamath, A., Zhang, Y., Marathe, P., Hunt, J.T., Lombardo, L.J., Fargnoli, J., and Borzilleri, R.M., Bioorg. Med. Chem. Lett., 2008, vol. 18, no. 11, p. 3224. doi  https://doi.org/10.1016/j.bmcl.2008.04.047 CrossRefGoogle Scholar
  3. 3.
    Hranjec, M., Sovic, I., Ratkaj, I., Pavlovic, G., Ilic, N., Valjalo, L., Pavelić, K., Kraljević Pavelić, S., and Karminski-Zamola, G., Eur. J. Med. Chem., 2013, vol. 59, p. 111. doi  https://doi.org/10.1016/j.ejmech.2012.11.009 CrossRefGoogle Scholar
  4. 4.
    Amedio, I.C., Jr., Lee, G. T., Prasad, K., and Repic, O., Synth. Commun., 1995, vol. 25, p. 2599. doi  https://doi.org/10.1080/00397919508011806 CrossRefGoogle Scholar
  5. 5.
    Borisova, I.A., Zubarev, A.A., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., 2018, vol. 67, no. 1, p. 168. doi  https://doi.org/10.1007/s11172-018-2054-2 CrossRefGoogle Scholar
  6. 6.
    Kabra, V., Meel, A., Mathur, R., and Kaushik, P., Phosphorus, Sulfur, Silicon, Relat. Elem., 2007, vol. 182, no. 6, p. 1403. doi  https://doi.org/10.1080/10426500601161056 CrossRefGoogle Scholar
  7. 7.
    Patil, R.S., Kokate, M.R., Salvi, P.P., and Kolekar, S.S., C. R. Chimie, 2011, vol. 14, no. 12, p. 1122. doi  https://doi.org/10.1016/j.crci.2011.07.009 CrossRefGoogle Scholar
  8. 8.
    Kim, D.G. and Uspenskaya, S.E., Izv. Vuzov. Ser. Khim. i Khim. Tekhnol., 1993, no. 9, p. 121.Google Scholar
  9. 9.
    Seethalakshmi, T., Venkatesan, P., Nallu, M., Lynch, D.E., and Thamotharan, S., Acta Crystallogr. (E), 2013, vol. 69, no. 6, p. 884. doi  https://doi.org/10.1107/S1600536813012452 Google Scholar
  10. 10.
    Kim, D.G., Berdnikova, E.V., and Slepukhin, P.A., Vestn. YuURGU. Ser. Khim., 2014, vol. 6, no. 4, p. 5.Google Scholar
  11. 11.
    Bakherad, M., Nasr-Isfahani, H., Keivanloo, A., and Doostmohammadi, N., Tetrahedron Lett., 2008, vol. 49, no. 23, p. 3819. doi  https://doi.org/10.1016/j.tetlet.2008.03.141 CrossRefGoogle Scholar
  12. 12.
    Paira, R., Maity, A., Mondal, S., Naskar, S., Sahu, K.B., Saha, P., Hazra, A., Padmanaban, E., Banerjee, S., and Mondal, N.B., Tetrahedron Lett., 2011, vol. 52, no. 14, p. 1653. doi  https://doi.org/10.1016/j.tetlet.2011.01.134 CrossRefGoogle Scholar
  13. 13.
    Viscomi, G.C., Campana, M., Folegatti, M., Cannata, V., Righi, P., and Rosini, G., WO Patent 122436, 2010, Canada.Google Scholar
  14. 14.
    Dolzhenko, A.V., Kolotova, N.V., Kozminykh, V.O., Chui, W.K., Heng, P.W.S., and Khrustalev, V.N., Heterocycles, 2004, vol. 63, no. 1, p. 55. doi  https://doi.org/10.3987/COM-03-9909 CrossRefGoogle Scholar
  15. 15.
    Kovalenko, N.V., Cherepakha, A.Yu., Kutrov, G.P., Shishkin, O.V., and Shishkina, S.V., Chem. Heterocycl. Compd., 2012, vol. 47, no. 10, p. 1280. doi  https://doi.org/10.1007/s10593-012-0903-8 CrossRefGoogle Scholar
  16. 16.
    Groselj, U., Bezensek, J., Meden, A., Svete, J., Stanovnik, B., Oblak, M., Anderluh, P.S., and Urleb, U., Heterocycles, 2008, vol. 75, no. 6, p. 1355. doi  https://doi.org/10.3987/COM-07-11303 CrossRefGoogle Scholar
  17. 17.
    Sucunza, D., Samadi, A., Chioua, M., Silva, D.B., Yunta, C., Infantes, L., Carmo Carreiras, M., Soriano, E., and Marco-Contelles, J., Chem. Commun., 2011, vol. 47, no. 17, p. 5043. doi  https://doi.org/10.1039/c1cc10641d CrossRefGoogle Scholar
  18. 18.
    Osheko, K.Yu., Kim, D.G., El’tsov, O.S., and Shtukina, T.S., Russ. J. Org. Chem., 2018, vol. 54, no. 9, p. 1406. doi  https://doi.org/10.1134/S1070428018090233 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • E. V. Kalita
    • 1
    Email author
  • D. G. Kim
    • 1
  • D. A. Rakhmatullina
    • 1
  • M. A. Pylneva
    • 1
  • E. M. Krynina
    • 1
  1. 1.South Ural State University (National Research University)ChelyabinskRussia

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