Skip to main content
SpringerLink
Log in

A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides

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

Abstract

The novel functionalized N,N′-[2-(arylsulfonamido)propane-1,3-diyl]bis(N-allylarylsulfonamide) and N,N′-[2-(methylsulfonamido)propane-1,3-diyl]bis(N-benzylarylsulfonamide) derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using substituted arylsulfonamides in the presence of sodium methoxide under catalyst-free condition in good yields.

Graphic 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. Singh GS (2016) Mini-Rev Med Chem 16:892

    Article  CAS  Google Scholar 

  2. McCoull W, Davis FA (2000) Synthesis 10:1347

    Article  Google Scholar 

  3. Yudin AK (2006) Aziridines and epoxied organic synthesis. Wiley-VCH, Weinheim

    Book  Google Scholar 

  4. Stankovic S, D’hooghe M, Catak S, Waroquier M, Van Speybroeck V, de Kimpe N, Ha H-J (2012) Chem Soc Rev 41:643

    Article  CAS  Google Scholar 

  5. Sweeney JB (2002) Chem Soc Rev 31:247

    Article  CAS  Google Scholar 

  6. Fringuell F, Piermatti O, Pizzo F, Vaccaro L (2003) Curr Org Chem 7:1661

    Article  Google Scholar 

  7. Olsen CA, Franzyk H, Jaroszewski JW (2007) Eur J Org Chem 11:1717

    Article  Google Scholar 

  8. Singh GS, D’hooghe M, de Kimpe N (2007) Chem Rev 107:2080

    Article  CAS  Google Scholar 

  9. Gensler WJ, Koehler WR (1962) J Org Chem 27:2754

    Article  CAS  Google Scholar 

  10. Thakur VV, Sudalai A (2003) Tetrahedron Lett 44:989

    Article  CAS  Google Scholar 

  11. Karikomi M, de Kimpe N (2000) Tetrahedron Lett 41:10295

    Article  CAS  Google Scholar 

  12. Gensler WH, Dheer SK (1981) J Org Chem 46:4051

    Article  CAS  Google Scholar 

  13. Karikomi M, D’hooghe M, Verniest G, de Kimpe N (2008) Org Biomol Chem 6:1902

    Article  CAS  Google Scholar 

  14. D’hooghe M, de Kimpe N (2004) Synlett 2:271

    Google Scholar 

  15. Han S-M, Ma S-H, Ha H-J, Lee WK (2008) Tetrahedron 64:11110

    Article  CAS  Google Scholar 

  16. Bergmeier SC, Seth PP (1997) J Org Chem 62:2671

    Article  CAS  Google Scholar 

  17. D’hooghe M, Kenis S, Vervisch K, Lategah C, Smith PJ, Chibale K, de Kimpe N (2011) Eur J Med Chem 46:579

    Article  Google Scholar 

  18. Wang L-W, Kang H-J, Chen IJ, Teng C-M, Lin C-N (2002) Bioorg Med Chem Lett 10:567

    Article  Google Scholar 

  19. Bair KW, Andrews CW, Tuttle RL, Knick VC, Cory M, Mckee DD (1991) J Med Chem 34:1983

    Article  CAS  Google Scholar 

  20. Ashwell MA, Solvibile WR, Han S, Largis E, Mulvey R, Tillet J (2001) Bioorg Med Chem Lett 11:3123

    Article  CAS  Google Scholar 

  21. Davis FA, Zhou P (1994) Tetrahedron Lett 35:7525

    Article  CAS  Google Scholar 

  22. Giordano C, Cavicchioli S, Levi S, Villa M (1991) J Org Chem 56:6114

    Article  CAS  Google Scholar 

  23. Clark JE, Fisher PA, Schumacher DP (1991) Synthesis 891

    Article  Google Scholar 

  24. Abbaspour Tehrani K, Van Nguyen T, Karikomi M, Rottiers M, de Kimpe N (2002) Tetrahedron 58:7145

    Article  Google Scholar 

Download references

Acknowledgements

We thank the Bushehr Branch, Islamic Azad University for support.

Author information

Authors and Affiliations

  1. Chemistry Department, Bushehr Branch, Islamic Azad University, PO Box 7519619555, Bushehr, Iran

    Fatemeh Azizi & Gholamhossein Khalili

Authors
  1. Fatemeh Azizi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gholamhossein Khalili
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gholamhossein Khalili.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1279 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Azizi, F., Khalili, G. A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides. Monatsh Chem 151, 261–265 (2020). https://doi.org/10.1007/s00706-019-02546-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-019-02546-9

Keywords

Search

Navigation