Skip to main content
SpringerLink
Log in

Efficient synthesis of 1-carbamatoalkyl-2-naphthols using Brønsted acidic ionic liquid as reusable catalyst

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

Abstract

Efficient synthesis of 1-carbamatoalkyl-2-naphthols can be carried out in the presence of halogen-free Brønsted acidic ionic liquid, synthesized from 1,4-diaza-bicyclo[2.2.2]octane (DABCO) and 1,4-butanesulfonate. A wide range of aldehydes and carbamates easily undergo condensation with 2-naphthol to afford the desired products in good to excellent yields. The present methodology offers several advantages, such as a simple work-up procedure and short reaction times. The catalyst can be recycled and reused without substantial reduction in catalytic activities.

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
Scheme 2
Scheme 3

Similar content being viewed by others

References:

  1. F. Nakatsubo, A.J. Cocuzza, D.E. Keeley, Y.J. Kishi, Am. Chem. Soc. 99, 4835–4836 (1977)

    Article  CAS  Google Scholar 

  2. H. Tanino, T. Nakata, Y. Kaneko, Y. Kishi, J. Am. Chem. Soc. 99, 2818–2819 (1977)

    Article  CAS  Google Scholar 

  3. A. Millar, K.-H. Kim, D.K. Minster, T. Ohgi, S.M. Hecht, J. Org. Chem. 51, 189–196 (1986)

    Article  CAS  Google Scholar 

  4. V. Snieckus, Chem. Rev. 90, 879–933 (1990)

    Article  CAS  Google Scholar 

  5. P. Anastas, N. Eghbali, Chem. Soc. Rev. 39, 301–312 (2010)

    Article  CAS  Google Scholar 

  6. T.E. Nielsen, S.L. Schreiber, Angew. Chem. Int. Ed. 47, 48–56 (2008)

    Article  CAS  Google Scholar 

  7. Y. Coquerel, T. Boddaert, M. Presset, D. Mailhol, J. Rodriguez, Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry (Wiley-VCH, Weinheim, 2010)

    Google Scholar 

  8. B.M. Trost, Acc. Chem. Res. 35, 695–705 (2002)

    Article  CAS  Google Scholar 

  9. P.A. Wender, V.A. Verma, T.J. Paxton, T.H. Pillow, Acc. Chem. Res. 41, 40–49 (2008)

    Article  CAS  Google Scholar 

  10. J. Zhu, H. Bienayme (eds.), Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Google Scholar 

  11. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, 2nd edn (Wiley-VCH, Weinheim, 2008)

    Google Scholar 

  12. B. Ni, A.D. Headley, Chem. Eur. J. 16, 4426–4436 (2010)

    Article  CAS  Google Scholar 

  13. N. Isambert, M.M. Sanchez Duque, J.-C. Plaquevent, Y. Genisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347–1357 (2011)

    Article  CAS  Google Scholar 

  14. T. Dingermann, D. Steinhilber, G. Folkers, Molecular Biology in Medicinal Chemistry (Wiley-VCH, Weinheim, 2004)

    Google Scholar 

  15. M. Dabiri, A.S. Delbari, A. Bazgir, Heterocycles 71, 543–548 (2007)

    Article  CAS  Google Scholar 

  16. H.R. Shaterian, A. Hosseinian, M. Ghashang, Tetrahedron Lett. 49, 5804–5806 (2008)

    Article  CAS  Google Scholar 

  17. H.R. Shaterian, A. Hosseinian, M. Ghashang, Synth. Commun. 39, 2560–2574 (2009)

    Article  CAS  Google Scholar 

  18. H.R. Shaterian, A. Hosseinian, M. Ghashang, Chin. J. Chem. 27, 821–824 (2009)

    Article  CAS  Google Scholar 

  19. M.M. Heravi, N. Tavakoli-Hoseini, F.F. Bamoharram, Green Chem. Lett. Rev. 3, 263–267 (2010)

    Article  CAS  Google Scholar 

  20. D. Kundu, A. Majee, A. Hajra, Catal. Commun. 11, 1157–1159 (2010)

    Article  CAS  Google Scholar 

  21. N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, Bull. Korean Chem. Soc. 32, 787–792 (2011)

    Article  CAS  Google Scholar 

  22. K.M. Deshmukh, Z.S. Qureshi, Y.P. Patil, B.M. Bhanage, Synth. Commun. 42, 93–101 (2012)

    Article  CAS  Google Scholar 

  23. H.R. Shaterian, A. Hosseinian, H. Yarahmadi, M. Ghashang, Lett. Org. Chem. 5, 290–295 (2008)

    Article  CAS  Google Scholar 

  24. X. Liang, Y. Wang, G. Gong, J. Yang, Catal. Commun. 10, 281–284 (2008)

    Article  CAS  Google Scholar 

  25. X. Liang, S. Gao, J. Yang, M. He, Catal. Lett. 125, 396–400 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We are grateful to Sistan and Baluchestan University Research Council for the partial support of this research.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran

    Hamid Reza Shaterian & Asghar Hosseinian

Authors
  1. Hamid Reza Shaterian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Asghar Hosseinian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hamid Reza Shaterian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaterian, H.R., Hosseinian, A. Efficient synthesis of 1-carbamatoalkyl-2-naphthols using Brønsted acidic ionic liquid as reusable catalyst. Res Chem Intermed 40, 3011–3019 (2014). https://doi.org/10.1007/s11164-013-1147-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1147-7

Keywords

Search

Navigation