Skip to main content
SpringerLink
Log in

Efficient Synthesis of 4H-Pyran and Spiro-Oxindole Derivatives Based on Al2O3/V2O5 Nanocomposite as Catalyst

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

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

A simple and eco-friendly catalytic alternative has been proposed for one-pot three-component synthesis of 4H-pyrane and spiro-oxindole derivatives, as two important classes of potentially bioactive compounds, in the presence of a catalytic amount of Al2O3/V2O5 nanocomposite. Good to excellent yields and short reaction times were obtained for both series of Al2O3/V2O5-catalyzed reactions. In addition, the Al2O3/V2O5 nanocatalyst can be reused without appreciable loss of activity. The obtained results suggest prospects of using Al2O3/V2O5 nanocomposite as potent heterogeneous catalyst in other syntheses.

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

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Multicomponent Reactions, Zhu, J. and Bienaymé, H., Eds., Weinheim: Wiley, 2005.

  2. Rostamnia, S., Alamgholiloo, H., and Jafari, M., Appl. Organomet. Chem., 2018, vol. 32, p. 4370. https://doi.org/10.1002/aoc.4370

    Article  CAS  Google Scholar 

  3. Maleki, A., Hajizadeh, Z., and Abbasi, H., Carbon Lett., 2018, vol. 27, p. 42. https://doi.org/10.5714/CL.2018.27.042

    Article  Google Scholar 

  4. Slobbe, P., Ruijter, E., and Orru, R.V.A., Med. Chem. Commun., 2012, vol. 3, p. 1189. https://doi.org/10.1039/c2md20089a

    Article  CAS  Google Scholar 

  5. Raj, T., Bhatia, R.K., Kapur, A., Sharma, M., Saxena, A.K., and Ishar, M.P.S., Eur. J. Med. Chem., 2010, vol. 45, p. 790. https://doi.org/10.1016/j.ejmech.2009.11.001

    Article  CAS  PubMed  Google Scholar 

  6. Hussein, A.H.M., Gad-El Kareem, M.A.M., ElAdasy, A.A.M., Khames, A.A., and Othman, I.M.M., Int. J. Org. Chem., 2012, vol. 2, p. 341. https://doi.org/10.4236/ijoc.2012.24047

    Article  CAS  Google Scholar 

  7. Khodairy, A., Ali, A.M., Aboelez, M.O., and El-Wassimy, M.T.,J. Heterocycl. Chem., 2017, vol. 54, p. 1442. https:/doi.org/10.1002/jhet.2730

    Article  CAS  Google Scholar 

  8. Kumar, A., Maurya, R.A., Sharma, S.A., Ahmad, P., Singh, A.B., Bhatia, G., and Srivastava, A.K., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 6447. https://doi.org/10.1016/j.bmcl.2009.09.031

    Article  CAS  PubMed  Google Scholar 

  9. Rueping, M., Sugiono, E., and Merino, E., Chem. Eur. J., 2008, vol. 14, p. 6329. https://doi.org/10.1002/chem.200800836

    Article  CAS  PubMed  Google Scholar 

  10. Capim, S.L., Gonçalves, G.M., dos Santos, G.C.M., Marinho, B.G., and Vasconcellos, M.L.A.A., Bioorg. Med. Chem., 2013, vol. 21, p. 6003. https://doi.org/10.1016/j.bmc.2013.07.041

    Article  CAS  PubMed  Google Scholar 

  11. Dutta, A.K., Gopishetty, B., Gogoi, S., Ali, S., Zhen, J., and Reith, M., Eur. J. Pharmacol., 2011, vol. 39, p. 671. https://doi.org/10.1016/j.ejphar.2011.09.162

    Article  CAS  Google Scholar 

  12. Mar’yasov, M. A., Sheverdov, V.P., Davydova, V.V., and Nasakin, O.E., Pharm. Chem. J., 2017, vol. 50, p. 798. https://doi.org/10.1007/s11094-017-1534-2

    Article  CAS  Google Scholar 

  13. Mar’yasov, M.A., Davydova, V.V., Sheverdov, V.P., Nasakin, O.E., and Gein, V.L., Pharm. Chem. J., 2016, vol. 50, p. 519. https://doi.org/10.1007/s11094-016-1480-4

    Article  CAS  Google Scholar 

  14. Shaabani, A., Ghadari, R., Sarvary, A., and Rezayan, A.H.,J. Org. Chem., 2009, vol. 74, p. 4372. https://doi.org/10.1021/jo9005427

    Article  CAS  PubMed  Google Scholar 

  15. Kumar, D., Reddy, V.B., Sharad, S., Dube, U., and Suman, K.A.,Eur. J. Med. Chem., 2009, vol. 44, p. 3805. https://doi.org/10.1016/j.ejmech.2009.04.017

    Article  CAS  PubMed  Google Scholar 

  16. Bhavanarushi, S., Kanakaiah, V., Yakaiah, E., Saddanapu, V., Addlagatta, A., and Rani, V.J., Med. Chem. Res., 2013, vol. 22, p. 2446. https://doi.org/10.1007/s00044-012-0239-z

    Article  CAS  Google Scholar 

  17. Erichsen, M.N., Huynh, T.H.V., Abrahamsen, B., Bastlund, J.F., Bundgaard, C., Monrad, O., Jensen, A.B., Nielsen, C.W., Frydenvang, K., Jensen, A.A., and Bunch, L., J. Med. Chem., 2010, vol. 53, p. 7180. https://doi.org/10.1021/jm1009154

    Article  CAS  PubMed  Google Scholar 

  18. Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Grundy, C.C., Labreque, D., Bubenick, M., Attardo, G., Denis, R., Lamothe, S., Gourdeau, H., Tseng, B., Kasibhatla, S., and Cai, S.X., J. Med. Chem., 2008, vol. 51, p. 417. https://doi.org/10.1021/jm7010657

    Article  CAS  PubMed  Google Scholar 

  19. Mahmoodi, M., Aliabadi, A., Emami, S., Safavi, M., Rajabalian, S., Mohagheghi, A.M., Khoshzaban, A., Kermani, A.S., Lamei, N., Shafiee, A., and Foroumadi, A., Arch. Pharm., 2010, vol. 343, p. 411. https://doi.org/10.1002/ardp.200900198

    Article  CAS  Google Scholar 

  20. Rottmann, M., McNamara, C., Yeung, B.K.S., Lee, M.C.S., Zou, B., Russell, B., Seitz, P., Plouffe, D.M., Dharia, N.V., Tan, J., Cohen, S.B., Spencer, K.R., Gonzalez-Paez, G.E., Lakshminarayana, S.B., Goh, A., Suwanarusk, R., Jegla, T., Schmitt, E.K., Beck, H.-P., Brun, R., Nosten, F., Renia, L., Dartois, V., Keller, T.H., Fidock, D.A., Winzeler, E.A., and Diagana, T.T.,Science, 2010, vol. 329, p. 1175. https://doi.org/10.1126/science.1193225

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Yeung, B.K.S., Zou, B., Rottmann, M., Lakshminarayana, S.B., Ang, S.H., Leong, S.Y., Tan, J., Wong, J., Keller-Maerki, S., Fischli, C., Goh, A., Schmitt, E.K., Krastel, P., Francotte, E., Kuhen, K., Plouffe, D., Henson, K., Wagner, T., Winzeler, E.A., Petersen, F., Brun, R., Dartois, V., Diagana, T.T., and Keller, T.H., J. Med. Chem., 2010, vol. 53, p. 5155. https://doi.org/10.1021/jm100410f

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Elnagdi, N.M.H. and Al-Hokbany, N.S., Molecules, 2012, vol. 17, p. 4300. https://doi.org/10.3390/molecules17044300

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Pandharpatte, M.S., Mulani, K.B., and Mohammed, N.N.G., J. Chin. Chem. Soc., 2012, vol. 59, p. 645. https://doi.org/10.1002/jccs.201100304

    Article  CAS  Google Scholar 

  24. El-Bayouki, K.A.M., Basyouni, W.M., Khatab, T.K., El-Basyoni, F.A., Hamed, A.R., and Mostafa, E.A., J. Heterocycl. Chem., 2014, vol. 51, p. 106. https://doi.org/10.1002/jhet.2019

    Article  CAS  Google Scholar 

  25. Sun, W-B., Zhang, P., Fan, J., Chen, S-H., and Zhang, Z-H.,Synth. Commun., 2010, vol. 40, p. 587. https://doi.org/10.1080/00397910903007079

    Article  CAS  Google Scholar 

  26. Pagadala, R., Maddila, S., and Jonnalagadda, S.B., J. Heterocycl. Chem., 2015, vol. 52, p. 1226. https://doi.org/10.1002/jhet.2125

    Article  CAS  Google Scholar 

  27. Khurana, J.M., Nand, B., and Saluja, P., J. Heterocycl. Chem., 2014, vol. 51, p. 618. https://doi.org/10.1002/jhet.1507

    Article  CAS  Google Scholar 

  28. Bihani, M., Bora, P.P., Bez, G., and Askari, H., C. R. Chim., 2013, vol. 16, p. 419. https://doi.org/10.1016/j.crci.2012.11.018

    Article  CAS  Google Scholar 

  29. Banerjee, S., Horn, A., Khatri, H., and Sereda, G., Tetrahedron Lett., 2011, vol. 52, p. 1878. https://doi.org/10.1016/j.tetlet.2011.02.031

    Article  CAS  Google Scholar 

  30. Bhattacharyya, P., Pradhan, K., Paul, S., and Das, A.R., Tetrahedron Lett., 2012, vol. 53, p. 4687. https://doi.org/10.1016/j.tetlet.2012.06.086

    Article  CAS  Google Scholar 

  31. Zhang, S-G., Yin, S-F., Wei, Y-D., Luo, S-L., and Au, C-T.,Catal. Lett., 2012, vol. 142, p. 608. https://doi.org/10.1007/s10562-012-0805-5

    Article  CAS  Google Scholar 

  32. Wang, L.M., Jiao, N., Qiu, J., Yu, J.J., Liu, J.Q., Guo, F.L., and Liu, Y., Tetrahedron, 2010, vol. 66, p. 339. https://doi.org/10.1016/j.tet.2009.10.091

    Article  CAS  Google Scholar 

  33. Raghuvanshi, D.S. and Singh, K.N., J. Heterocycl. Chem., 2010, vol. 47, p. 1323. https://doi.org/10.1002/jhet.451

    Article  CAS  Google Scholar 

  34. Dandia, A., Parewa, V., Kumar Jain, A., and Rathore, K.S.,Green Chem., 2011, vol. 13, p. 2135. https://doi.org/10.1039/C1GC15244K

    Article  CAS  Google Scholar 

  35. Rad-Moghadam, K. and Youseftabar-Miri, L., Tetrahedron, 2011, vol. 67, p. 5693. https://doi.org/10.1016/j.tet.2011.05.077

    Article  CAS  Google Scholar 

  36. Maheshwar Rao, B., Niranjan Reddy, G., Vijaikumar Reddy, T., Prabhavathi Devi, B.L.A., Prasad, R.B.N., Yadav, J.S., and Subba Reddy, B.V.,Tetrahedron Lett., 2013, vol. 54, p. 2466. https://doi.org/10.1016/j.tetlet.2013.02.089

    Article  CAS  Google Scholar 

  37. Karmakar, B., Nayak, A., and Banerji, J., Tetrahedron Lett., 2012, vol. 53, p. 5004. https://doi.org/10.1016/j.tetlet.2012.07.030

    Article  CAS  Google Scholar 

  38. Lee, Y.R. and Hari, G.S., Synthesis., 2010, vol. 2010, p. 453. https://doi.org/10.1055/s-0029-1217116

    Article  CAS  Google Scholar 

  39. Hassani, H., Zakerinasab, B., and Nozarie, A., Asian J. Green Chem., 2018, vol. 2, p. 59. https://doi.org/10.22631/ajgc.2017.101572.1032

    Article  CAS  Google Scholar 

  40. Rahimizadeh, M., Bazazan, T., Shiri, A., Bakavoli, M., and Hassani, H., Chin. Chem. Lett., 2011, vol. 22, p. 435. https://doi.org/10.1016/j.cclet.2010.10.052

    Article  CAS  Google Scholar 

  41. Hassani, H., Nasseri, M.A., Zakerinasab, B., and Rafiee, F.,Appl. Organomet. Chem., 2016, vol. 30, p. 408. https://doi.org/10.1002/aoc.3447

    Article  CAS  Google Scholar 

  42. Zakerinasab, B., Nasseri, M.A., Hassani, H., and Samieadel, M.M.,Res. Chem. Intermed., 2016, vol. 42, p. 3169. https://doi.org/10.1007/s11164-015-2204-1

    Article  CAS  Google Scholar 

  43. Hassani, H., Zakerinasab, B., Nasseri, M.A., and Shavakandi, M.,RSC Adv., 2016, vol. 6, p. 17560. https://doi.org/10.1039/C5RA24252E

    Article  CAS  Google Scholar 

  44. Akbari, A., Hakimi, M., Hassani, H., Vahedi, H., and Ghambari Khosh, A., Int. J. ChemTech Res., 2012, vol. 4, p. 729. https://www.researchgate.net/publication/237049413

    CAS  Google Scholar 

  45. Hakimi, M., Feizi, N., Hassani, H., Vahedi, H., and Thomas, P.S.,Synth. Commun., 2010, vol. 40, p. 725. https://doi.org/10.1080/00397910903013705

    Article  CAS  Google Scholar 

  46. Hassani, H., Zakerinasab, B., and Hossien Poor, H., Appl. Organomet. Chem., 2017, vol. 32, p. 3945. https://doi.org/10.1002/aoc.3945

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to Payame Noor University for partial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Iran

    H. Hassani, Z. Jahani & H. H. Poor

Authors
  1. H. Hassani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Z. Jahani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. H. Poor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to H. Hassani.

Ethics declarations

The authors declare 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

Hassani, H., Jahani, Z. & Poor, H.H. Efficient Synthesis of 4H-Pyran and Spiro-Oxindole Derivatives Based on Al2O3/V2O5 Nanocomposite as Catalyst. Russ J Org Chem 56, 491–497 (2020). https://doi.org/10.1134/S1070428020030197

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020030197

Keywords:

Search

Navigation