Skip to main content
SpringerLink
Log in

Solvent-free one-pot synthesis of 1-carbamatoalkyl-2-naphthols by a tin tetrachloride catalyzed multicomponent reaction

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An efficient one-pot synthesis of 1-carbamatoalkyl-2-naphthols using tin tetrachloride as a catalyst for the three-component condensation reaction of 2-naphthol, aldehydes, and carbamates under thermal, solvent-free conditions is described. This new approach has advantages such as mild conditions, short reaction time, high yield, simple work-up, and an inexpensive catalyst.

Graphical Abstract

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

Similar content being viewed by others

References

  1. Csütörtöki R, Szatmári I, Mándi A, Kurtán T, Fülöp F (2011) Synlett 22:1940

    Google Scholar 

  2. Knapp S (1995) Chem Rev 95:1859

    Article  CAS  Google Scholar 

  3. Juaristi E (1997) Enantioselective synthesis of β-amino acids. Wiley, New York

  4. Dingermann T, Steinhilber D, Folkers G (2004) Molecular biology in medicinal chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  5. Shen AY, Tsai CT, Chen CL (1999) Eur J Med Chem 34:877

    Article  CAS  Google Scholar 

  6. Wang M, Liang Y (2011) Monatsh Chem 142:153

    Article  CAS  Google Scholar 

  7. Green W, Wuts PGM (1999) Protecting groups in organic synthesis, 2nd edn. Wiley, New York

    Book  Google Scholar 

  8. Mosslemin MH, Nateghi MR, Mohebat R (2008) Monatsh Chem 139:1247

    Article  CAS  Google Scholar 

  9. Shaterian HR, Hosseinian A, Ghashang MA (2008) Tetrahedron Lett 49:5804

    Article  CAS  Google Scholar 

  10. Tavakoli-Hoseini N, Heravi MM, Bamoharran FF, Davoodnia A (2011) Bull Korean Chem Soc 32:787

    Article  CAS  Google Scholar 

  11. Reza SH, Asghar H, Majid G (2009) Chin J Chem 27:821

    Article  Google Scholar 

  12. Heravi MM, Tavakoli-Hoseini N, Bamoharram FF (2010) Green Chem Lett Rev 3:263

    Article  CAS  Google Scholar 

  13. Shaterian HR, Hosseinian A, Ghashang M (2009) Synth Commun 39:2560

    Article  CAS  Google Scholar 

  14. Kundu D, Majee A, Hajra A (2010) Catal Commun 11:1157

    Article  CAS  Google Scholar 

  15. Tamaddon F, Bistgani JM (2011) Synlett 22:2947

    Article  Google Scholar 

  16. Deshmukh KM, Qureshi ZS, Patil YP, Bhanage BM (2012) Synth Commun 42:93

    Article  CAS  Google Scholar 

  17. Yarahmadi H, Shaterian HR (2012) J Chem Res 36:52

    Google Scholar 

  18. Shafiee MRM, Moloudi R, Ghashang M (2011) J Chem Res 35:622

    Google Scholar 

  19. Zare A, Yousofi T, Moosavi-Zare AR (2012) RSC Adv 2:7988

    Article  CAS  Google Scholar 

  20. Zare A, Akbarzadeh S, Foroozani E, Kaveh H, Moosavi-Zare AR, Hasaninejad A, Mokhlesi M, Beyzavi MH, Zolfigol MA (2012) J Sulfur Chem 33:259

    Article  CAS  Google Scholar 

  21. Khazaei A, Zolfigol MA, Moosavi-Zare AR, Abi F, Zare A, Kaveh H, Khakyzadeh V, Kazem-Rostami M, Parhami A, Torabi-Monfared H (2013) Tetrahedron 69:212

    Article  CAS  Google Scholar 

  22. Csütörtöki R, Szatmári I, Koch A, Heydenreich M, Kleinpeter E, Fülöp F (2011) Tetrahedron 67:8564

    Article  Google Scholar 

  23. Bigdeli MA, Rahmati A, Abbasi-Ghadim H, Mahdavinia GH (2007) Tetrahedron Lett 48:4575

    Article  CAS  Google Scholar 

  24. Dujardin G, Martel A, Brown E (1998) Tetrahedron Lett 39:8647

    Article  CAS  Google Scholar 

  25. Jing HW, Nguyen ST (2007) J Mol Catal A 261:12

    Google Scholar 

  26. Kita Y, Matsuda S, Inoguchi R, Ganesh JK, Fujioka H (2005) Tetrahedron Lett 46:89

    Article  CAS  Google Scholar 

  27. Takeya T, Doi H, Ogata T, Okamoto I, Kotani E (2004) Tetrahedron 60:9049

    Article  CAS  Google Scholar 

  28. Savushkina GP, Ivanov VV, Yenikolopyan NS (1975) Vysokomol Soyed A17:865

    Google Scholar 

  29. Wang M, Liang Y, Zhang TT, Gao JJ (2012) Chem Nat Compd 48:185

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research work was financially supported by the Education Committee of Liaoning Province of China (No. L2011198).

Author information

Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Food Safety, Bohai University, Jinzhou, 121000, China

    Min Wang, Qing L. Wang, Shuang Zhao & Xin Wan

Authors
  1. Min Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Qing L. Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shuang Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xin Wan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Min Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, M., Wang, Q.L., Zhao, S. et al. Solvent-free one-pot synthesis of 1-carbamatoalkyl-2-naphthols by a tin tetrachloride catalyzed multicomponent reaction. Monatsh Chem 144, 975–980 (2013). https://doi.org/10.1007/s00706-013-0927-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-0927-5

Keywords

Search

Navigation