Skip to main content
SpringerLink
Log in

A green one-pot synthesis of α-amino nitrile derivatives via Strecker reaction in deep eutectic solvents

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

Abstract

In this work, the synergic effect of choline chloride/urea as a deep eutectic solvent was investigated in the three-component Strecker reaction for the synthesis of α-amino nitriles that contain a thiazole moiety. A simple separation, easy to set up, eco-friendly, and short time for purification of products in high yields without using chromatography are the advantages of this catalytic protocol.

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

Fig. 1

Similar content being viewed by others

References

  1. Smith EL, Abbott AP, Ryder KS (2014) Chem Rev 114:11060

    Article  CAS  Google Scholar 

  2. Wagle DV, Zhao H, Baker GA (2014) Acc Chem Res 47:2299

    Article  CAS  Google Scholar 

  3. Zhang Q, Vigier KDO, Royer S, Jerome F (2012) Chem Soc Rev 41:7108

    Article  CAS  Google Scholar 

  4. Tang B, Row KH (2013) Monatsh Chem 144:1427

    Article  CAS  Google Scholar 

  5. Mamajanov I, Engelhart AE, Bean HD, Hud NV (2010) Angew Chem Int Ed 49:6310

    Article  CAS  Google Scholar 

  6. Abbott AP, Harris RC, Ryder KS, D’Agostino C, Gladden LF, Mantle MD (2011) Green Chem 13:82

    Article  CAS  Google Scholar 

  7. Dai Y, van Spronsen J, Witkamp G-J, Verpoorte R, Choi YH (2013) Anal Chim Acta 766:61

    Article  CAS  Google Scholar 

  8. Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004) J Am Chem Soc 126:9142

    Article  CAS  Google Scholar 

  9. Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Chem Commun 1:70–71

    Article  Google Scholar 

  10. Abbott AP, Capper G, Davies DL, McKenzie KJ, Obi SU (2006) J Chem Eng Data 51:1280

    Article  CAS  Google Scholar 

  11. Pena-Pereira F, Namieśnik J (2014) Chemsuschem 7:1784

    Article  CAS  Google Scholar 

  12. del Monte F, Carriazo D, Serrano MC, Gutiérrez MC, Ferrer ML (2014) Chemsuschem 7:999

    Article  Google Scholar 

  13. Francisco M, van den Bruinhorst A, Kroon MC (2012) Green Chem 14:2153

    Article  CAS  Google Scholar 

  14. Zhang Z-H, Zhang X-N, Mo L-P, Li Y-X, Ma F-P (2012) Green Chem 14:1502

    Article  CAS  Google Scholar 

  15. Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M, Ross G (2008) Synthesis 24:4007–4011

    Article  Google Scholar 

  16. Toure BB, Hall DG (2009) Chem Rev 109:4439

    Article  CAS  Google Scholar 

  17. Ramezanpour S, Panahi A, Rominger F (2018) Monatsh Chem 149:625

    Article  CAS  Google Scholar 

  18. Weber L (2002) Curr Med Chem 9:2085

    Article  CAS  Google Scholar 

  19. Domling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  CAS  Google Scholar 

  20. Strecker A (1850) Liebigs Ann Chem 75:27

    Article  Google Scholar 

  21. Reimann E, Ettmayr C (2004) Monatsh Chem 135:1289

    Article  CAS  Google Scholar 

  22. Saaby S, Fang X, Gathergood N, Jørgensen KA (2000) Angew Chem Int Ed 39:4114

    Article  CAS  Google Scholar 

  23. Ishitani H, Komiyama S, Hasegawa Y, Kobayashi S (2000) J Am Chem Soc 122:762

    Article  CAS  Google Scholar 

  24. Ganem B (2009) Acc Chem Res 42:463

    Article  CAS  Google Scholar 

  25. Benner SA, Kim H-J, Kim M-J, Ricardo A (2010) Cold Spring Harb Perspect Biol. https://doi.org/10.1101/cshperspect.a003467

    Article  PubMed  PubMed Central  Google Scholar 

  26. Corey EJ, Gin DY, Kania RS (1996) J Am Chem Soc 118:9202

    Article  CAS  Google Scholar 

  27. Krishnamurthy R, Snieckus V (2017) Synlett 28:27

    Google Scholar 

  28. Lown JW, Joshua AV, Lee JS (1982) Biochemistry 21:419

    Article  CAS  Google Scholar 

  29. Paget CJ, Kisner K, Stone RL, DeLong DC (1969) J Med Chem 12:1010

    Article  CAS  Google Scholar 

  30. Aoki K, Ijima T, Kamiyama H, Kamiko K, Terauchi Y (2015) Expert Opin Pharmacother 16:1749

    Article  CAS  Google Scholar 

  31. Ahrén B (2009) Best Pract Res Clin Endocrinol Metab 23:487

    Article  Google Scholar 

  32. Parker ET, Zhou M, Burton AS, Glavin DP, Dworkin JP, Krishnamurthy R, Fernández FM, Bada JL (2014) Angew Chem Int Ed 53:8132

    Article  CAS  Google Scholar 

  33. Sefat MN, Saberi D, Niknam K (2011) Catal Lett 141:1713

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  35. Hernández JG, Turberg M, Schiffers I, Bolm C (2016) Chem Eur J 22:14513

    Article  Google Scholar 

  36. He HX, Du DM (2014) Eur J Org Chem 28:6190

    Article  Google Scholar 

  37. Shaabani A, Hooshmand SE, Afaridoun H (2017) Monatsh Chem 148:711

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support from the Islamic Azad University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Firoozabad Branch, Islamic Azad University, Firoozabad, Fars, Iran

    Abdolaziz Bahrani & Zahed Karimi-Jaberi

Authors
  1. Abdolaziz Bahrani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zahed Karimi-Jaberi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zahed Karimi-Jaberi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1757 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bahrani, A., Karimi-Jaberi, Z. A green one-pot synthesis of α-amino nitrile derivatives via Strecker reaction in deep eutectic solvents. Monatsh Chem 150, 303–307 (2019). https://doi.org/10.1007/s00706-018-2313-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2313-9

Keywords

Search

Navigation