Skip to main content
SpringerLink
Log in

Solvent and catalyst-free synthesis of some new aminonaphthoquinones from lawsone, ninhydrin and heteroaryl amines

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

An efficient and easy method has been developed for the preparation of some new aminonaphthoquinone derivatives from a one-pot three-component condensation of 2-hydroxy-1,4-naphthoquinone, ninhydrin and heteroaryl amines under catalyst and solvent-free conditions at 75 °C. The protocol describes in situ generated imine as intermediate from the condensation reaction of ninhydrin with heteroaryl amines followed by the addition of 2-hydroxynaphthalene-1,4-dione to the imine, afforded the desired products. The operational simplicity of the procedure, shorter reaction times, simple workup procedure, clean reaction, easy purification of products by nonchromatographic methods, environmentally friendly conditions and high yields make this method much attractive.

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 1

Similar content being viewed by others

References

  1. D.C. Mcmillan, S.D. Sarvate, J.E. Oatis Jr., D.J. Jollow, Toxicol. Sci. 2, 647 (2004)

    Article  Google Scholar 

  2. J. Araldi, S.S. Guterres, Infarma 17, 78 (2005)

    Google Scholar 

  3. R. Pradhan, P. Dandawate, A. Vyas, S. Padhye, B. Biersack, R. Schobert, A. Ahmad, F.H. Sarkar, Curr. Drug Targets 13, 1777 (2012)

    Article  CAS  Google Scholar 

  4. A. Kosmalska, M. Zaborski, A. Masek, Przem. Chem. 89, 420 (2010)

    CAS  Google Scholar 

  5. R.R. Korac, K.M. Khambholja, Pharmacogn. Rev. 5, 164 (2011)

    Article  Google Scholar 

  6. R. Andoong, H. Chihchiang, Environ. Sci. Technol. 39, 7460 (2005)

    Article  Google Scholar 

  7. A. Ostovari, S.M. Hoseinieh, M. Peikari, S.R. Shadizadeh, S.J. Hashemi, Corros. Sci. 51, 1935 (2009)

    Article  CAS  Google Scholar 

  8. Y.M. Hijji, B. Barare, Y. Zhang, Sensors Actuat. B Chem. 169, 106 (2012)

    Article  CAS  Google Scholar 

  9. S. Ruhemann, Trans. Chem. Soc. 97, 1438 (1910)

    Article  CAS  Google Scholar 

  10. M. Friedman, J. Agric. Food Chem. 52, 385 (2004)

    Article  CAS  Google Scholar 

  11. A. Sinhababu, S. Basu, H. Dey, Res. Chem. Intermed. 41, 2785 (2015)

    Article  CAS  Google Scholar 

  12. G.M. LaPorte, R.S. Ramotowski, J. Forensic. Sci. 48, 658 (2003)

    PubMed  Google Scholar 

  13. L. Schwarz, I. Frerichs, J. Forensic. Sci. 47, 1274 (2002)

    Article  CAS  Google Scholar 

  14. P. Nagaraja, M.S. Hemantah Kumar, H.S. Yathirajan, J.S. Prakash, Anal. Sci. 18, 1027 (2002)

    Article  CAS  Google Scholar 

  15. M. Pavia, A.J. Trujillo, B. Guamis, V. Ferragut, J. Dairy Sci. 83, 1441 (2000)

    Article  CAS  Google Scholar 

  16. M. Moulin, C. Deleu, F.R. Larher, A. Bouchereau, Anal. Biochem. 308, 320 (2002)

    Article  CAS  Google Scholar 

  17. G. Mohammadi Ziarani, N. Lashgari, F. Azimian, H.G. Kruger, P. Gholamzadeh, ARKIVOC 6, 1 (2015)

    Google Scholar 

  18. T.T. Guimaraes, F.R. Maria do Carmo, J.S. Lanza, M.N. Melo, L. Rubens, I.M. de Melo, E.B. Diogo, V.F. Ferreira, C.A. Camara, W.O. Valenca, R.N. de Oliveira, F. Frezard, E.N. da Silva Jr, Eur. J. Med. Chem. 63, 523 (2013)

  19. M. Arundhati, C. Dipak, R. Mithun, Indian J. Pharm. Educ. Res. 52, 472 (2018)

    CAS  Google Scholar 

  20. A. Ahmad, K. Mahal, S. Padhye, F.H. Sarkar, R. Schobert, B. Biersack, J. Saudi. Chem. Soc. 21, 105 (2017)

    Article  CAS  Google Scholar 

  21. A.P. Neves, C.C. Barbosa, S.J. Greco, M.D. Vargas, L.C. Visentin, C.B. Pinheiro, A.S. Mangrich, J.P. Barbosa, G.L. da Costae, J. Braz. Chem. Soc. 20, 712 (2009)

    Article  CAS  Google Scholar 

  22. C. Festus, A.C. Ekennia, A.A. Osowole, L.O. Olasunkanmi, D.C. Onwudiwe, O.T. Ujam, Res. Chem. Intermed. 44, 5857 (2018)

    Article  CAS  Google Scholar 

  23. N.M.F. Lima, C.S. Correia, P.A.L. Ferraz, A.V. Pinto, M.C.R.F. do Pinto, A.E.G. Santana, M.O.F. Goulart, J. Braz. Chem. Soc. 13, 822 (2002)

    Article  CAS  Google Scholar 

  24. J.F. Allochio Filho, L.L. Roldi, M. Delarmelina, R.G. Fiorot, J.T. Andrade, Á.A. Aleixo, R.S. Carvalho, M.G.F. Araújo, J.M.S. Ferreira, A.G. Taranto, W. Romao, S.J. Greco, J. Braz. Chem. Soc. 27, 2127 (2016)

    CAS  Google Scholar 

  25. A.F.L. Vilela, B.M. Frugeri, A.L.F. Sarria, R.O.S. Kitamura, J.B. Fernandes, M.F.G.F. Silva, Q.B. Cass, C.L. Cardoso, J. Braz. Chem. Soc. 27, 535 (2016)

    Google Scholar 

  26. K. Mahal, A. Ahmad, F. Schmitt, J. Lockhauserbäumer, K. Starz, R. Pradhan, S. Padhye, F.H. Sarkar, W.S. Koko, R. Schobert, K. Ersfeld, B. Biersack, Eur. J. Med. Chem. 126, 421 (2017)

    Article  CAS  Google Scholar 

  27. C.P.P. de Mello, N.S. Sardoux, L. Terra, L.C. Amorim, M.D. Vargas, G.B. da Silva, H.C. Castro, V.A. Giongo, L.F. Madeira, I.C.N.P. Paixao, Antivir. Ther. 21, 507 (2016)

    Article  Google Scholar 

  28. M. Dabiri, Z. Noroozi Tisseh, A. Bazgir, Dyes Pigm. 89, 63 (2011)

    Article  CAS  Google Scholar 

  29. H.R. Tavakoli, S.M. Moosavi, A. Bazgir, Res. Chem. Intermed. 41, 3041 (2015)

    Article  CAS  Google Scholar 

  30. A. Olyaei, M. Sadeghpour, M. Khalaj, RSC Adv. 10, 30265 (2020)

    Article  CAS  Google Scholar 

  31. A. Olyaei, M.S. Shahsavari, M. Sadeghpour, Res. Chem. Intermed. 44, 943 (2018)

    Article  CAS  Google Scholar 

  32. A. Olyaei, R. Mohammad Ebrahimi, A. Adl, M. Sadeghpour, Chem. Heterocycl Compd. 55, 1104 (2019)

    Article  Google Scholar 

  33. F. Noruzian, A. Olyaei, R. Hajinasiri, Res. Chem. Intermed. 45, 4383 (2019)

    Article  CAS  Google Scholar 

  34. R. Khoeiniha, A. Olyaei, M. Saraei, J. Heterocyclic Chem. 54, 1746 (2017)

    Article  CAS  Google Scholar 

  35. R. Khoeiniha, A. Olyaei, M. Saraei, Synth. Commun. 48, 155 (2018)

    Article  CAS  Google Scholar 

  36. A. Olyaei, M. Saraei, R. Khoeiniha, Synlett 29, 1589 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the Research Council of Payame Noor University for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Payame Noor University (PNU), PO BOX 19395-4697, Tehran, Iran

    Abolfazl Olyaei & Neda Taheri

  2. Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, Iran

    Mahdieh Sadeghpour

Authors
  1. Abolfazl Olyaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Neda Taheri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mahdieh Sadeghpour
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abolfazl Olyaei.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 3,045 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Olyaei, A., Taheri, N. & Sadeghpour, M. Solvent and catalyst-free synthesis of some new aminonaphthoquinones from lawsone, ninhydrin and heteroaryl amines. Res Chem Intermed 47, 1211–1219 (2021). https://doi.org/10.1007/s11164-020-04325-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04325-2

Keywords

Search

Navigation