N-acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes in the synthesis of 3-(1H-1,2,4-triazol-3-yl)-3H-pyrrole-4-carbonitriles

Abstract

Reaction with phenylhydrazine of 3Н-pyrroles spirobound to a furan ring, N-acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes, occurs with a diasteroselective formation of previously unknown derivatives of 1,2,4-triazole: 5-amino-3-(5-alkyl-1-phenyl-1H-1,2,4-triazol-3-yl)-2-morpholin-4-yl-3H-pyrrole-4-carbonitriles.

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

References

  1. 1.

    Küçükgüzel, Ş.G. and Çıkla-Süzgün, P., Eur. J. Med. Chem., 2015, vol. 97, p. 830.

    Article  Google Scholar 

  2. 2.

    Maddila, S., Pagadala, R., and Jonnalagadda, S.B., Lett. Org. Chem., 2013, vol. 10, p. 693.

    CAS  Article  Google Scholar 

  3. 3.

    Kaur, R., Dwivedi, A.R., Kumar, B., and Kumar, V., Anticancer Agents Med. Chem., 2016, vol. 16, p. 465.

    CAS  Article  Google Scholar 

  4. 4.

    Kamboj, V.K., Verma, P.K., Dhanda, A., and Ranjan, S., Cent. Nerv. Syst. Agents Med. Chem., 2015, vol. 15, p. 17.

    CAS  Article  Google Scholar 

  5. 5.

    Kochikyan, T.V., Samvelyan, M.A., Arutyunyan, E.V., Arutyunyan, V.S., Avetisyan, A.A., Malakyan, M.G., Vardevanyan, L.A., and Badzhinyan, S.A., Pharm. Chem. J., 2011, vol. 44, p. 525. doi 10.1007/s11094-011-0509-y

    CAS  Article  Google Scholar 

  6. 6.

    Gençer, H.K., Çevik, U.A., Levent, S., Saglýk, B.N., Korkut, B., Özkay, Y., Iigin, S., and Öztürk, Y., Molecules, 2017, vol. 22, p. 507.

    Article  Google Scholar 

  7. 7.

    Al-Soud, Y.A., Marchais-Oberwinkler, S., Frotscher, M., and Hartmann, R.W., Arch. Pharm., 2012, vol. 345, p. 610.

    CAS  Article  Google Scholar 

  8. 8.

    Yang, L.P., Keam, S.J., and Keating, G.M., Drugs, 2007, vol. 67, p. 2211.

    CAS  Article  Google Scholar 

  9. 9.

    Salehi, S., Saljooghi, A.Sh., and Shiri, A., Eur. J. Pharm., 2016, vol. 781, p. 209.

    CAS  Article  Google Scholar 

  10. 10.

    Belikov, M.Yu., Ershov, O.V., Lipovskaya, I.V., Fedoseev, S.V., and Nasakin, O.E., Russ. J. Org. Chem., 2013, vol. 49, p. 864. doi 10.1134/S1070428013060110

    CAS  Article  Google Scholar 

  11. 11.

    Ershov, O.V., Nasakin, O.E., and Belikov, M.Yu., RF Patent no. 2475489, 2013.

    Google Scholar 

  12. 12.

    Belikov, M.Yu., Ievlev, M.Yu., Belikova, I.V., Ershov, O.V., Tafeenko, V.A., and Surazhskaya, M.D., Chem. Heterocycl. Compd., 2015, vol. 51, p. 518. doi 10.1007/s10593-015-1731-4

    CAS  Article  Google Scholar 

  13. 13.

    Belikov, M.Yu., Ershov, O.V., Lipovskaya, I.V., Fedoseev, S.V., Lipin, K.V., and Nasakin, O.E., Russ. J. Org. Chem., 2013, vol. 49, p. 1195. doi 10.1134/S1070428013080162

    CAS  Article  Google Scholar 

  14. 14.

    Belikov, M.Yu., Belikova, I.V., Ershov, O.V., Fedoseev, S.V., and Nasakin, O.E., Russ. J. Org. Chem., 2016, vol. 52, p. 1312. doi 10.1134/S1070428016090104

    CAS  Article  Google Scholar 

  15. 15.

    Padmavathi, V., Radha, L.T., Mahesh, K., and Padmaja, A., Chem. Pharm. Bull., 2009, vol. 57, p. 1200.

    CAS  Article  Google Scholar 

  16. 16.

    Cirrincione, G., Almerico, A.M., Grimaudo, S., Diana, P., Mingoia, F., Barraja, P., and Misuraca, F., Farmaco, 1996, vol. 51, p. 49.

    CAS  Google Scholar 

  17. 17.

    Sheldrick, G.M., Acta Cryst., 2008, vol. A64, p. 112.

    Article  Google Scholar 

  18. 18.

    Brandenburg, K., DIAMOND, Release 2.1d, Bonn, Germany: Crystal Impact, 2000.

    Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to M. Yu. Belikov.

Additional information

Original Russian Text © M.Yu. Belikov, I.V. Belikova, O.V. Ershov, S.V. Fedoseev, V.A. Tafeenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 11, pp. 1659–1663.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Belikov, M.Y., Belikova, I.V., Ershov, O.V. et al. N-acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes in the synthesis of 3-(1H-1,2,4-triazol-3-yl)-3H-pyrrole-4-carbonitriles. Russ J Org Chem 53, 1696–1700 (2017). https://doi.org/10.1134/S107042801711015X

Download citation