Skip to main content
SpringerLink
Log in

Al@Cu@TiO2 Nanocomposite: A Novel Recyclable Heterogeneous Catalyst for the Preparation of Chromenes

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

Abstract

A convenient and efficient one-pot procedure for the synthesis of pyrano[3,2-c]chromenes has been developed via three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and malononitrile in the presence of a catalytic amount of nano-titanium oxide doped with aluminum and copper salts (Al@Cu@TiO2) as a novel nanocatalyst. The catalyst was prepared via the reaction of titanium(IV) isopropoxide, Al(NO3)3, and Cu(NO3)2 in aqueous methanol. The proposed protocol offers various advantages such as shorter reaction times, use of a heterogeneous catalyst, and high yield of products in combination with simple experimental and workup procedures. The catalyst can be recovered and reused for at least five runs without any significant impact on the yields.

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

Fig. 1.
Scheme
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

Similar content being viewed by others

REFERENCES

  1. Mahmoodi, N.O., Khazaei, Z., and Mohammadi Zeydi, M., J. Iran. Chem. Soc., 2017, vol. 14, p. 1889. https://doi.org/10.1007/s13738-017-1128-7

    Article  CAS  Google Scholar 

  2. Ashjari, M., Garmroodi, M., Amiri Asl, F., Emam­pour, M., Yousefi, M., Pourmohammadi Lish, M., Habibi, Z., and Mohammadi, M., Process Biochem., 2020, vol. 90, p. 156. https://doi.org/10.1016/j.procbio.2019.11.002

    Article  CAS  Google Scholar 

  3. Wu, X.F., Neumann, H., and Beller, M., Chem. Rev., 2013, vol. 113, p. 1. https://doi.org/10.1021/cr300100s

    Article  CAS  Google Scholar 

  4. Mungra, D.C., Patel, M.P., Rajani, D.P., and Patel, R.G., Eur. J. Med. Chem., 2011, vol. 46, p. 4192. https://doi.org/10.1016/j.ejmech.2011.06.022

    Article  CAS  Google Scholar 

  5. Fu, Z.-Y., Jin, Q.-H., Qu, Y.-L., and Guan, L.-P., Bioorg. Med. Chem. Lett., 2019, vol. 29, p. 1909. https://doi.org/10.1016/j.bmcl.2019.05.051

    Article  CAS  Google Scholar 

  6. Saher, L., Makhloufi-Chebli, M., Dermeche, L., Dermeche, S., Boutemeur-Khedis, B., Rabia, C., Hamdi, M., and Silva, A.M.S., Tetrahedron, 2018, vol. 74, p. 872. https://doi.org/10.1016/j.tet.2018.01.009

    Article  CAS  Google Scholar 

  7. Sidorenko, A.Y., Kravtsova, A.V., Warna, J., Aho, A., Heinmaa, I., Ilina, I.V., Ardashov, O.V., Volcho, K.P., Salakhutdinov, N.F., Murzin, D.Yu., and Agabekov, V.E., Mol. Catal., 2018, vol. 453, p. 139. https://doi.org/10.1016/j.mcat.2018.05.007

    Article  CAS  Google Scholar 

  8. Zhang, W.-H., Chen, S., Liu, X.-L., Lin, B., Liu, X.-W., and Zhou, Y., Bioorg. Med. Chem. Lett., 2020, vol. 30, article ID 127410. https://doi.org/10.1016/j.bmcl.2020.127410

  9. Manouchehrizadeh, E., Mostoufi, A., Tahanpesar, E., and Fereidoonnezhad, M., Comput. Biol. Chem., 2019, vol. 80, p. 463. https://doi.org/10.1016/j.compbiolchem.2019.05.010

    Article  CAS  Google Scholar 

  10. Zghab, I., Trimeche, B., Ben Mansour, M., Hassine, M., Touboul, D., and Ben Jannet, H., Arab. J. Chem., 2017, vol. 10, p. S2651. https://doi.org/10.1016/j.arabjc.2013.10.008

  11. Kumar, M.S.L., Singh, J., Manna, S.K., Maji, S., Konwar, R., and Panda, G., Bioorg. Med. Chem. Lett., 2018, vol. 28, p. 778. https://doi.org/10.1016/j.bmcl.2017.12.065

    Article  CAS  Google Scholar 

  12. Jadhav, A.M., Krishnammagari, S.K., Kim, J.T., and Jeong, Y.T., Tetrahedron, 2017, vol. 73, p. 5163. https://doi.org/10.1016/j.tet.2017.07.008

    Article  CAS  Google Scholar 

  13. Irgashev, R.A., Sosnovskikh, V.Ya., Kalinovich, N., Kazakova, O., and Röschenthaler, G.-V., Tetrahedron Lett., 2009, vol. 50, p. 4903. https://doi.org/10.1016/j.tetlet.2009.06.067

    Article  CAS  Google Scholar 

  14. Looker, J.H., McMechan, J.H., and Mader, J.W., J. Org. Chem., 1978, vol. 43, p. 2344. https://doi.org/10.1021/jo00406a008

    Article  CAS  Google Scholar 

  15. Wen, S.S., Wang, J., Luo, Y.M., and Yang, H., Tetrahedron, 2014, vol. 70, p. 9314. https://doi.org/10.1016/j.tet.2014.10.045

    Article  CAS  Google Scholar 

  16. Wang, H.-J., Lu, J., and Zhang, Z.-H., Monatsh. Chem., 2010, vol. 141, p. 1107. https://doi.org/10.1007/s00706-010-0383-4

    Article  CAS  Google Scholar 

  17. Zhang, G., Zhang, Y., Yan, J., Chen, R., Wang, S., Ma, Y., and Wang, R., J. Org. Chem., 2012, vol. 77, p. 878. https://doi.org/10.1021/jo202020m

    Article  CAS  Google Scholar 

  18. Khurana, J.M. and Kumar, S., Tetrahedron Lett., 2009, vol. 50, p. 4125. https://doi.org/10.1016/j.tetlet.2009.04.125

    Article  CAS  Google Scholar 

  19. Abdolmohammadi, S. and Balalaie, S., Tetrahedron Lett., 2007, vol. 48, p. 3299. https://doi.org/10.1016/j.tetlet.2007.02.135

    Article  CAS  Google Scholar 

  20. Seifi, M. and Sheibani, H., Catal. Lett., 2008, vol. 126, p. 275. https://doi.org/10.1007/s10562-008-9603-5

    Article  CAS  Google Scholar 

  21. Shaabani, A., Samadi, S., Badri, Z., and Rahmati, A., Catal. Lett., 2005, vol. 104, p. 39. https://doi.org/10.1007/s10562-005-7433-2

    Article  CAS  Google Scholar 

  22. Heravi, M.M., Jani, B.A., Derikvand, F., Bamo­harram, F.F., and Oskooie, H.A., Catal. Commun., 2008, vol. 10, p. 272. https://doi.org/10.1016/j.catcom.2008.08.023

    Article  CAS  Google Scholar 

  23. Roudbaraki, S.J., Mansoor, S.S., and Ghashang, M., Polycyclic Aromat. Compd., 2021, vol. 41, p. 211. https://doi.org/10.1080/10406638.2019.1576746

    Article  CAS  Google Scholar 

  24. Mohammadi, R. and Kassaee, M.Z., J. Mol. Catal. A: Chem., 2013, vol. 380, p. 152. https://doi.org/10.1016/j.molcata.2013.09.027

    Article  CAS  Google Scholar 

  25. Reddy, M.V., Kumar, B.S., Lim, K.T., Cho, B.G., and Jeong, Y.T., Tetrahedron Lett., 2016, vol. 57, p. 476. https://doi.org/10.1016/j.tetlet.2015.12.061

    Article  CAS  Google Scholar 

  26. Puri, S., Kaur, B., Parmar, A., and Kumar, H., Ultrason. Sonochem., 2009, vol. 16, p. 705. https://doi.org/10.1016/j.ultsonch.2009.04.002

    Article  CAS  Google Scholar 

  27. Soltani, S., Montazeri, N., Heravi, M.M., and Zeydi, M.M., Russ. J. Org. Chem., 2020, vol. 56, p. 884. https://doi.org/10.1134/S1070428020050231

    Article  CAS  Google Scholar 

  28. Shiroud Ghorbani, S., Montazeri, N., Zeydi, M.M., and Ghane, M., Russ. J. Org. Chem., 2021, vol. 57, p. 605. https://doi.org/10.1134/S1070428021040151

    Article  Google Scholar 

  29. Kalantarian, R., Montazeri, N., Mohammadi Zeydi, M., Hatam, A., and Pizzi, A., Eur. J. Wood Wood Prod., 2021, vol. 79, p. 863. https://doi.org/10.1007/s00107-021-01662-w

    Article  CAS  Google Scholar 

  30. Zeydi, M.M. and Mahmoodi, N., Int. J. Nano Dimens., 2016, vol. 7, p. 174. https://doi.org/10.7508/ijnd.2016.02.010

    Article  CAS  Google Scholar 

  31. Meng, Y., Nanomaterials, 2015, vol. 23, p. 1124. https://doi.org/10.3390/nano5021124

    Article  CAS  Google Scholar 

  32. Narushima, T., Tsukamoto, H., and Yonezawa, T., AIP Adv., 2012, vol. 2, article ID 042113. https://doi.org/10.1063/1.4759498

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tonekabon Branch, Islamic Azad University, 46841-49588, Tonekabon, Iran

    H. Khodadad & M. Mohammadi Zeydi

Authors
  1. H. Khodadad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Mohammadi Zeydi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Mohammadi Zeydi.

Ethics declarations

The authors declared no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khodadad, H., Zeydi, M.M. Al@Cu@TiO2 Nanocomposite: A Novel Recyclable Heterogeneous Catalyst for the Preparation of Chromenes. Russ J Org Chem 58, 1466–1473 (2022). https://doi.org/10.1134/S1070428022100128

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022100128

Keywords:

Search

Navigation