Skip to main content
SpringerLink
Log in

Preparation of Silica-Based Ionic Liquid an Efficient and Recyclable Catalyst for One-Pot Synthesis of α-Aminonitriles

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Preparation of N-(3-silicapropyl) imidazolium hydrogen sulfate ([Sipim]HSO4) as a heterogeneous acidic ionic liquid is described. This heterogeneous ionic liquid was used as catalyst for the synthesis of α-aminonitriles by a one-pot condensation of aldehydes, amines, and trimethylsilyl cyanide at room temperature. Catalyst could be recycled for several times without any additional treatment.

Graphical Abstract

A simple and efficient procedure for the preparation of silica-based acidic ionic liquid ([Sipim]HSO4) is described. This heterogeneous solid acid is employed as a catalyst for the synthesis of a-amino nitriles at room temperature.

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
Fig. 1
Fig. 2
Scheme 2

Similar content being viewed by others

References

  1. Wasserscheid P, Welton T (2007) Ionic liquids in synthesis, 2nd edn. Wiley-VCH, Weinheim

    Book  Google Scholar 

  2. Keim W, Korth W, Wasserscheid P (2000) WO 016,902 Al, March 30

  3. Wasserscheid P, Sesing M, Korth W (2002) Green Chem 4:134

    Article  CAS  Google Scholar 

  4. Gupta N, Sonu GL, Kad J, Singh (2007) Catal Commun 8:1323

    Article  CAS  Google Scholar 

  5. Xu DQ, Yang WL, Luo SP, Wang BT, Wu M, Xu ZY (2007) Eur J Org Chem 6:1007–1012

    Google Scholar 

  6. Khosropour AR (2008) Can J Chem 86:264

    Article  CAS  Google Scholar 

  7. Wang W, Cheng W, Shao L, Yang J (2008) Catal Lett 121:77

    Article  CAS  Google Scholar 

  8. Hajipour AR, Rajaei A, Ruoho AE (2009) Tetrahedron Lett 50:708

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  10. Niknam K, Damya M (2009) J Chin Chem Soc 56:659

    CAS  Google Scholar 

  11. Niknam K, Zolfigol MA, Saberi D, Khonbazi M (2009) Chin J Chem 27:1548

    Article  CAS  Google Scholar 

  12. Tajik H, Niknam K, Sarrafan M (2011) Synth Commun 41:2103

    Article  CAS  Google Scholar 

  13. Qiao K, Hagiwara H, Yokoyama C (2006) J Mol Catal A 246:65

    Article  CAS  Google Scholar 

  14. Sugimura R, Qiao K, Tomida D, Yokoyama C (2007) Catal Commun 8:770

    Article  CAS  Google Scholar 

  15. Chrobok A, Baj S, Pudlo W, Jarzebski A (2009) Appl Catal A 366:22

    Article  CAS  Google Scholar 

  16. Strecker A (1850) Ann Chem Pharm 75:27

    Article  Google Scholar 

  17. Shafran YM, Bakulev VS, Mokrushin VS (1989) Russ Chem Rev 58:148

    Article  Google Scholar 

  18. March J (1995) Advanced organic chemistry, 4th edn. Wiley, New York, p 965

    Google Scholar 

  19. Weinstock LM, Davis P, Handelsman B, Tull R (1967) J Org Chem 32:2823

    Article  CAS  Google Scholar 

  20. Matier WL, Owens DA, Comer WT, Dietchman D, Ferguson HC, Seidehamel RJ, Young JR (1973) J Med Chem 16:901

    Article  CAS  Google Scholar 

  21. Mai K, Patil G (1984) Tetrahedron Lett 25:4583

    Article  CAS  Google Scholar 

  22. El-Ahl AAS (2003) Synth Commun 33:989

    Article  CAS  Google Scholar 

  23. Yadav JS, Reddy BVS, Eswaraiah B, Srinivas M (2004) Tetrahedron 60:1767

    Article  CAS  Google Scholar 

  24. Karimi B, Safari AA (2008) J Organomet Chem 693:2967

    Article  CAS  Google Scholar 

  25. Reddy BM, Thirupathi B, Patil MK (2009) J Mol Catal A 307:154

    Article  CAS  Google Scholar 

  26. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Singh S, Suresh E, Jasra RV (2008) Tetrahedron Lett 49:640

    Article  CAS  Google Scholar 

  27. Ranu BC, Dey SS, Hajra S (2002) Tetrahedron 58:2529

    Article  CAS  Google Scholar 

  28. Wang SH, Zhao LF, Du ZM (2006) Chin J Chem 24:135

    Article  CAS  Google Scholar 

  29. Mojtahedi MM, Abaee S, Alishiri T (2009) Tetrahedron Lett 50:2322

    Article  CAS  Google Scholar 

  30. Shaabani A, Maleki A, Soudi MR, Mofakham H (2009) Catal Commun 10:945

    Article  CAS  Google Scholar 

  31. Yadav JS, Reddy BVS, Eshwaraiah B, Srinivas M, Vishnumurthy P (2003) New J Chem 27:462

    Article  CAS  Google Scholar 

  32. Chen WY, Lu J (2005) Synlett 2293–2296

  33. Karimi B, Zareyee D (2009) J Mater Chem 19:8665

    Article  CAS  Google Scholar 

  34. Niknam K, Saberi D, Nouri Sefat M (2010) Tetrahedron Lett 51:2959

    Article  CAS  Google Scholar 

  35. Kassaee MZ, Masrouri H, Movahedi F (2011) Appl Catal A 395:28

    Article  CAS  Google Scholar 

  36. Leblanc J, Gibson HW (1992) Tetrahedron Lett 33:6295

    Article  CAS  Google Scholar 

  37. Heydari A, Fatemi P, Alizadeh AA (1998) Tetrahedron Lett 39:3049

    Article  CAS  Google Scholar 

  38. Das B, Ramu R, Ravikanth B, Reddy KR (2006) Synthesis 1419–1422

Download references

Acknowledgment

The authors are thankful to Persian Gulf University Research Council for partial support of this study.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Sciences, Persian Gulf University, 75169, Bushehr, Iran

    Maryam Nouri Sefat, Dariush Saberi & Khodabakhsh Niknam

Authors
  1. Maryam Nouri Sefat
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dariush Saberi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Khodabakhsh Niknam
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Khodabakhsh Niknam.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1270 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nouri Sefat, M., Saberi, D. & Niknam, K. Preparation of Silica-Based Ionic Liquid an Efficient and Recyclable Catalyst for One-Pot Synthesis of α-Aminonitriles. Catal Lett 141, 1713–1720 (2011). https://doi.org/10.1007/s10562-011-0696-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-011-0696-x

Keywords

Search

Navigation