Skip to main content
SpringerLink
Log in

Ionic liquid 1-(4-nitritobutyl)-3-methylimidazolium chloride as a new reagent for the efficient N-nitrosation of secondary amines under mild conditions

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

Abstract

1-(4-Nitritobutyl)-3-methylimidazolium chloride has been developed as a new reagent for efficient nitrosation of secondary amines at 0 °C to room temperature. A variety of N-nitrosamines were prepared in excellent yields by use of this task-specific ionic liquid under mild and heterogeneous conditions.

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

Scheme 1

Similar content being viewed by others

References

  1. Gong K, Fang D, Wang H-L, Zhou X-L, Liu Z-L (2009) Dyes Pigm 80:30

    Article  CAS  Google Scholar 

  2. Le Z-G, Chen Z-C, Hu Y, Zheng Q-G (2004) Synthesis 2809

  3. Yue C, Mao A, Wei Y, Lü M (2008) Catal Commun 9:1571

    Article  CAS  Google Scholar 

  4. Wang L, Li H, Li P (2009) Tetrahedron 65:364

    Article  CAS  Google Scholar 

  5. Macfarlane DR, Pringle JM, Johansson KM, Forsyth SA, Forsyth M (2006) Chem Commun 1905

  6. Paun C, Barklie J, Goodrich P, Gunaratne HQN, McKeown A, Pârvulescu VI, Hardacre C (2007) J Mol Catal A Chem 269:64

    Article  CAS  Google Scholar 

  7. Tajik H, Niknam K, Parsa F (2009) J Iran Chem Soc 6:159

    CAS  Google Scholar 

  8. Bhosale RS, Sarda SR, Giram RP, Raut DS, Parwe SP, Ardhapure SS, Pawar RP (2009) J Iran Chem Soc 6:519

    CAS  Google Scholar 

  9. Hajipour AR, Rafiee F, Ruoho AE (2010) J Iran Chem Soc 7:114

    CAS  Google Scholar 

  10. Valizadeh H, Shockravi A (2009) Heteroatom Chem 20:284

    Article  CAS  Google Scholar 

  11. Valizadeh H, Gholipour H (2010) Synth Commun 40:1477

    Article  CAS  Google Scholar 

  12. Valizadeh H (2010) Heteroatom Chem 21:78

    Article  CAS  Google Scholar 

  13. Valizadeh H, Shockravi A (2009) Synth Commun 39:4341

    Article  CAS  Google Scholar 

  14. Garcia-Rio L, Leis JR, Issglesias E (1997) J Org Chem 62:4712

    Article  CAS  Google Scholar 

  15. Nudelman NS, Bonatti AE (2000) Synlett 1825 (references cited therein)

  16. Vogel AI, Tatchell AR, Furnis BS, Hannaford AJ, Smith PWG (1986) Vogels text book of practical organic chemistry, 4th edn. Longman, London

    Google Scholar 

  17. Olah GA (1979) Aldrichimica Acta 12:43

    CAS  Google Scholar 

  18. Lecher H, Siefhen W (1926) Chem Ber 59:2594

    Google Scholar 

  19. Makhora NN, Karpov GA, Mikhailyuk AN, Bova AE, Khmel’nitskii LI, Novikov SS (1978) lzv Akad Nauk SSSR Ser Khim 1:226

    Google Scholar 

  20. Chang SK, Harrington GW, Rothstein M, Shergalis WA, Swern D, Vohra SK (1979) Cancer Res 39:3871

    CAS  Google Scholar 

  21. Castedo L, Riguera R, Vázquez MP (1983) J Chem Soc Chem Commun 301

  22. Nakajima M, Warner JC, Anselme JP (1984) Tetrahedron Lett 25:2619

    Article  CAS  Google Scholar 

  23. Fanning JC, Keefer LK, Larry K (1987) J Chem Soc Chem Commun 955

  24. Zolfigol MA (1999) Synth Commun 29:905

    Article  CAS  Google Scholar 

  25. Zolfigol MA, Ghaemi E, Madrakian E, Kiany-Borazjani M (2000) Synth Commun 30:2057

    Article  CAS  Google Scholar 

  26. Zolfigol MA, Shirini F, Ghorbani Choghamarani A, Taqiannasab A, Keypour H, Salehzadeh S (2000) J Chem Res (S) 420

  27. Zolfigol MA, Zebarjadian MH, Chehardoli G, Keypour H, Salehzadeh S, Shamsipur M (2001) J Org Chem 66:3619

    Article  CAS  Google Scholar 

  28. Zolfigol MA, Shirini F, Choghamarani AG (2002) Synth Commun 32:1809

    Article  CAS  Google Scholar 

  29. Zarchi MAK, Noei J (2009) J Appl Polym Sci 114:2134

    Article  CAS  Google Scholar 

  30. Roche D, Lardy C, Tournier L, Prunier M, Valeur E (2010) Tetrahedron Lett 51:2277

    Article  CAS  Google Scholar 

  31. Valizadeh H, Shomali A (2010) Dyes Pigm. doi:10.1016/j.dyepig.2010.11.010

  32. Hou J-Y, Wang Y-L, Wang J-Y (2003) J Chem Res (S) 626

  33. Smith JRL, Nee MW, Noar JB, Bruice TC (1984) J Chem Soc Perkin Trans 2 255

  34. Iranpoor N, Firouzabadi H, Nowrouzi N (2008) Tetrahedron Lett 49:4242

    Article  CAS  Google Scholar 

  35. Seebach D, Enders D (1975) Chem Ber 108:1293

    Article  CAS  Google Scholar 

  36. Loeppky RN, Elomari S (2000) J Org Chem 65:96

    Article  CAS  Google Scholar 

  37. Gowenlock BG, Pfab J, Young VM (1997) J Chem Soc Perkin Trans 2 915

    Google Scholar 

  38. Giumanini AG, Verardo G (1997) Can J Chem 75:469

    Article  CAS  Google Scholar 

  39. Yu Y, Ostresh JM, Houghten RA (2003) J Org Chem 68:183

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support of this work by the research affairs of Azarbaijan University of Tarbiat Moallem is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran

    Hassan Valizadeh, Hamid Gholipour & Ashkan Shomali

Authors
  1. Hassan Valizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hamid Gholipour
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ashkan Shomali
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hassan Valizadeh.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Valizadeh, H., Gholipour, H. & Shomali, A. Ionic liquid 1-(4-nitritobutyl)-3-methylimidazolium chloride as a new reagent for the efficient N-nitrosation of secondary amines under mild conditions. Monatsh Chem 143, 467–470 (2012). https://doi.org/10.1007/s00706-011-0574-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0574-7

Keywords

Search

Navigation