Skip to main content
SpringerLink
Log in

Synthesis of Functionalized Bicyclic Compounds Based on 2-(1-Arylethylidene)malononitriles

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

Abstract

New tetrahydroisoquinoline-5,7-dicarbonitrile derivatives have been synthesized by piperazine hydrate-catalyzed reaction of acetoacetanilide with 2-(1-arylethylidene)malononitriles (Knoevenagel condensation products of acetophenones and malononitrile) in aqueous ethanol at room temperature. The product structure was confirmed by NMR spectra and X-ray analysis of 1,6-diamino-4a-methyl-3-oxo-2,8-diphenyl-2,3,4,4a-tetrahydroisoquinoline-5,7-dicarbonitrile.

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

References

  1. Galán, A., Moreno, L., Párraga, J., Serrano, Á., Sanz, M.J., Cortes, D., and Cabedo, N., Bioorg. Med. Chem., 2013, vol. 21, p. 3221. https://doi.org/10.1016/j.bmc.2013.03.042

    Article  Google Scholar 

  2. Liu, X.H., Zhu, J., Zhou, A., Song, B.A., Zhu, H.L., Bai, L.Sh., Bhadury, P.S., and Pan, C.X., Bioorg. Med. Chem., 2009, vol. 17, p. 1207. https://doi.org/10.1016/j.bmc.2008.12.034

    Article  Google Scholar 

  3. Iwasa, K., Moriyasu, M., Tachibana, Y., Kim, H.S., Wataya, Y., Wiegrebe, W., Bastow, K.F., Cosentino, L.M., Kozuka, M., and Lee, K.H., Bioorg. Med. Chem., 2001, vol. 9, p. 2871. https://doi.org/10.1016/s0968-0896(01)00154-7

    Article  CAS  Google Scholar 

  4. Tiwari, R.K., Singh, D., Singh, J., Chhillar, A.K., Chandra, R., and Verma, A.K., Eur. J. Med. Chem., 2006, vol. 41, p. 40. https://doi.org/10.1016/j.ejmech.2005.10.010

    Article  CAS  Google Scholar 

  5. Dabholkar, V.V. and Tripathi, D.R., J. Heterocycl. Chem., 2011, vol. 48, p. 529. https://doi.org/10.1002/jhet.245

    Article  CAS  Google Scholar 

  6. Yu, Y., Tu, M.S., Jiang, B., Wang, Sh.L., and Tu, Sh.J., Tetrahedron Lett., 2012, vol. 53, p. 5071. https://doi.org/10.1016/j.tetlet.2012.07.008

    Article  CAS  Google Scholar 

  7. Wang, X.W., Li, P., Xiao, H., Zhu, Sh.Zh., and Zhao, G., Tetrahedron, 2011, vol. 67, p. 7618. https://doi.org/10.1016/j.tet.2011.07.007

    Article  CAS  Google Scholar 

  8. Korotaev, V.Yu., Barkov, A.Yu., Kutyashev, I.B., Safrygin, A.V., and Sosnovskikh, V.Ya., Tetrahedron, 2014, vol. 70, p. 3584. https://doi.org/10.1016/j.tet.2014.03.105

    Article  CAS  Google Scholar 

  9. Villemin, D., Belhadj, Z., Cheikh, N., Choukchou-Braham, N., Bar, N., and Lohier, J.F., Tetrahedron Lett., 2013, vol. 54, p. 1664. https://doi.org/10.1016/j.tetlet.2013.01.021

    Article  CAS  Google Scholar 

  10. Alizadeh, A., Hosseini, S.Y., Sedighian, H., Bayat, F., Zhu, Z., and Dusek, M., Tetrahedron, 2015, vol. 71, p. 7885. https://doi.org/10.1016/j.tet.2015.08.033

    Article  CAS  Google Scholar 

  11. Xue, D., Li, J., Zhang, Z.T., and Deng, J.G., J. Org. Chem., 2007, vol. 72, p. 5443. https://doi.org/10.1021/jo070766i

    Article  CAS  Google Scholar 

  12. Battye, T.G., Kontogiannis, L., Johnson, O., Powell, H.R., and Leslie, A.G.W., Acta Crystallogr., Sect. D, 2011, vol. 67, p. 271. https://doi.org/10.1107/S0907444910048675

    Article  CAS  Google Scholar 

  13. Evans, P., Acta Crystallogr., Sect. D, 2006, vol. 62, p. 72. https://doi.org/10.1107/S0907444905036693

    Article  Google Scholar 

  14. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  Google Scholar 

Download references

Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.1154.2017/4.6).

Author information

Authors and Affiliations

  1. Baku State University, Baku, 1148, Azerbaijan

    F. N. Naghiyev, I. G. Mamedov, Kh. A. Asadov & A. M. Maharramov

  2. Kurchatov Institute National Research Center, Moscow, 123182, Russia

    P. V. Dorovatovskii

  3. People’s Friendship University of Russia, Moscow, 117198, Russia

    V. N. Khrustalev

  4. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russia

    V. N. Khrustalev

Authors
  1. F. N. Naghiyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. G. Mamedov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kh. A. Asadov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. V. Dorovatovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. N. Khrustalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. M. Maharramov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to F. N. Naghiyev, P. V. Dorovatovskii or V. N. Khrustalev.

Additional information

Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1933–1937.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Naghiyev, F.N., Mamedov, I.G., Asadov, K.A. et al. Synthesis of Functionalized Bicyclic Compounds Based on 2-(1-Arylethylidene)malononitriles. Russ J Org Chem 55, 1967–1970 (2019). https://doi.org/10.1134/S1070428019120273

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019120273

Keywords

Search

Navigation