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Synthesis of Water-Soluble α-Aminopyrroles, 1-(2-Amino-1H-pyrrol-3-yl)pyridinium Chlorides

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Abstract

A method for the synthesis of water-soluble α-aminopyrroles, 1-(2-amino-1H-pyrrol-3-yl)pyridinium chlorides, by the reaction 1-(cyanomethyl)pyridinium chloride with alkyl 3-aryl-2H-azirine-2-carboxylates was developed.

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REFERENCES

  1. Bąchor, U. and Mączyński, M., Molecules, 2021, vol. 26, p. 438. https://doi.org/10.3390/molecules26020438

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Li Petri, G., Spano, V., Spatola, R., Holl, R., Raimondi, M. V., Barraja, P., and Montalbano, A., Eur. J. Med. Chem., 2020, vol. 208, p. 112783. https://doi.org/10.1016/j.ejmech.2020.112783

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Boichuk, S., Galembikova, A., Bikinieva, F., Dunaev, P., Aukhadieva, A., Syuzov, K., Zykova, S., Igidov, N., Ksenofontov, A., and Bocharov, P., Molecules, 2021, vol. 26, p. 616. https://doi.org/10.3390/molecules26030616

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Boichuk, S., Galembikova, A., Dunaev, P., Micheeva, E., Novikova, M., Khromova, N., and Kopnin, P., Anti-Cancer Drugs, 2019, vol. 30, p. 475. https://doi.org/10.1097/CAD.0000000000000753

    Article  CAS  PubMed  Google Scholar 

  5. Corona, A., Onnis, V., Deplano, A., Bianco, G., Demurtas, M., Distinto, S., Cheng, Y.-C., Alcaro, S., Esposito, F., and Tramontano, E., Pathog. Dis., 2017, vol. 75, p. ftx078. https://doi.org/10.1093/femspd/ftx078

  6. McGeary, R.P., Tan, D.T.C., Selleck, C., Pedroso, M.M., Sidjabat, H.E., Schenk, G., Eur. J. Med. Chem., 2017, vol. 137, p. 351. https://doi.org/10.1016/j.ejmech.2017.05.061

    Article  CAS  PubMed  Google Scholar 

  7. Guo, H., Eleftheriadis, N., Rohr-Udilova, N., Dömling, A., and Dekker, F.J., Eur. J. Med. Chem., 2017, vol. 139, p. 633. https://doi.org/10.1016/j.ejmech.2017.07.047

    Article  CAS  PubMed  Google Scholar 

  8. Olivier, W.J., Smith, J.A., and Bissember, A.C., Org. Biomol. Chem., 2018, vol. 16, p. 1216. https://doi.org/10.1039/C7OB03144K

    Article  CAS  PubMed  Google Scholar 

  9. Guchhait, S.K., Sisodiya, S., Saini, M., Shah, Y.V., Kumar, G., Daniel, D.P., Hura, N., and Chaudhary, V., J. Org. Chem., 2018, vol. 83, p. 5807. https://doi.org/10.1021/acs.joc.8b00465

    Article  CAS  PubMed  Google Scholar 

  10. Qi, X., Xiang, H., He, Q., and Yang, C., Org. Lett., 2014, vol. 16, p. 4186. https://doi.org/10.1021/ol5018855

    Article  CAS  PubMed  Google Scholar 

  11. Yu, W., Chen, W., Liu, S., Shao, J., Shao, Z., Lin, H., and Yu, Y., Tetrahedron, 2013, vol. 69, p. 1953. https://doi.org/10.1016/j.tet.2012.11.041

    Article  CAS  Google Scholar 

  12. Frolova, L.V., Evdokimov, N.M., Hayden, K., Malik, I., Rogelj, S., Kornienko, A., and Magedov, I.V., Org. Lett., 2011, vol. 13, p. 1118. https://doi.org/10.1021/ol103149b

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Wamhoff, H. and Wehling, B., Synthesis, 1976, vol. 8, p. 51. https://doi.org/10.1055/s-1976-23958

    Article  Google Scholar 

  14. Galenko, E.E., Linnik, S.A., Khoroshilova, O.V., Novikov, M.S., and Khlebnikov, A.F., J. Org. Chem., 2019, vol. 84, p. 11275. https://doi.org/10.1021/acs.joc.9b01634

    Article  CAS  PubMed  Google Scholar 

  15. Su, Z., Wang, S., Luo, N., and Wang, C., Synlett, 2020, vol. 31, p. 1022. https://doi.org/10.1055/s-0040-1707466

    Article  CAS  Google Scholar 

  16. Agafonova, A.V., Funt, L.D., Novikov, M.S., and Khlebnikov, A.F., Org. Biomol. Chem., 2021, vol. 19, p. 1976. https://doi.org/10.1039/d1ob00053e

    Article  CAS  PubMed  Google Scholar 

  17. Funt, L.D., Novikov, M.S., and Khlebnikov, A.F., Tetrahedron, 2020, vol. 76, p. 131415; https://doi.org/10.1016/j.tet.2020.131415

    Article  CAS  Google Scholar 

  18. Galenko, E.E., Khlebnikov, A.F., and Novikov, M.S., Chem. Heterocycl. Compd., 2016, vol. 52, p. 637. https://doi.org/10.1007/s10593-016-1944-1

    Article  CAS  Google Scholar 

  19. Galenko, E.E., Tomashenko, O.A., Khlebnikov, A.F., and Novikov, M.S., Org. Biomol. Chem., 2015, vol. 13, p. 9825. https://doi.org/10.1039/c5ob01537e

    Article  CAS  PubMed  Google Scholar 

  20. Huuskonen, J., Comb. Chem. High Throughput Scr., 2001. vol. 4. p. 311. https://doi.org/10.2174/1386207013331147

    Article  CAS  Google Scholar 

  21. Proença, M.F. and Costa, M., Tetrahedron, 2010, vol. 66, p. 4542. https://doi.org/10.1016/j.tet.2010.04.059

    Article  CAS  Google Scholar 

  22. Dydio, P., Lichosyt, D., and Jurczak, J., Chem. Soc. Rev., 2011, vol. 40, p. 2971. https://doi.org/10.1039/c1cs15006e

    Article  CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The work was performed using the equipment of the “Magnetic Resonance Research Center” and “Chemical Analysis and Materials Research Center” of the Research Park of St. Petersburg State University.

Funding

The work was financially supported by the Russian Science Foundation (project no. 19-13-00039).

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Correspondence to A. F. Khlebnikov.

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No conflict of interest was declared by the authors.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1143–1148 https://doi.org/10.31857/S0044460X21070192.

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Galenko, E.E., Kaminskiy, N.A., Novikov, M.S. et al. Synthesis of Water-Soluble α-Aminopyrroles, 1-(2-Amino-1H-pyrrol-3-yl)pyridinium Chlorides. Russ J Gen Chem 91, 1424–1428 (2021). https://doi.org/10.1134/S1070363221070239

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  • DOI: https://doi.org/10.1134/S1070363221070239

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