Skip to main content
Log in

Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines

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

Abstract

An efficient organocatalytic approach for the synthesis of 1,3-oxathiolanes and 1,3-thiazolidines is reported. In this methodology, conjugated base of nitromethane was employed as a potential organocatalyst to promote cyclization reaction between strained heterocyclic compounds and heterocumulenes at ambient conditions.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Yudin AK (ed) (2006) Aziridines and Epoxides in Organic Synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  2. Hu XE (2004) Tetrahedron 60:2701

    Article  CAS  Google Scholar 

  3. ShenYM, Duan WL, Shi M (2003) J Org Chem 68:1559

  4. Nozaki K, Nakano K, Hiyama T (1999) J Am Chem Soc 121:11008

    Article  CAS  Google Scholar 

  5. Tascedda P, Dunach E (2000) Chem Commun 6:449

    Article  Google Scholar 

  6. Hancock MT, Pinhas AR (2003) Tetrahedron Lett 44:5457

    Article  CAS  Google Scholar 

  7. Evans DA, Downey CW, Hubbs JL (2003) J Am Chem Soc 125:8706

    Article  CAS  Google Scholar 

  8. McCoull W, Davisb FA (2000) Synthesis 10:1347

    Article  Google Scholar 

  9. Ferraris D, Cox C, Lectka T (1998) J Org Chem 63:4568

    Article  CAS  Google Scholar 

  10. Khumtaveeporn K, Alper H (1995) Acc Chem Res 28:414

    Article  CAS  Google Scholar 

  11. Fan RH, Hou XL, Dai LX (2004) J Org Chem 69:689

    Article  CAS  Google Scholar 

  12. Evans DA, Downey CW, Hubbs JL (2003) J Am Chem Soc 125:8706

    Article  CAS  Google Scholar 

  13. Murugana R, Anbazhaganb S, Narayanan S (2009) Eur J Med Chem 44:3272

    Article  Google Scholar 

  14. Yavari I, Ghazanfarpour-Darjani M, Hossaini Z, Sabbaghan M, Hosseini N (2008) Synlett 6:889

    Article  Google Scholar 

  15. Yavari I, Ghazanfarpour-Darjani M (2014) J Sulfur Chem 35:477

    Article  CAS  Google Scholar 

  16. Samzadeh-Kermani A (2014) Monatsh Chem 145:611

    Article  CAS  Google Scholar 

  17. Sriharshaa SN, Satishb S, Shashikantha S, Raveeshab KA (2006) Bioorg Med Chem 14:7476

    Article  Google Scholar 

  18. Wu JY, Luo ZB, Dai LX, Hou XL (2008) J Org Chem 73:9137

    Article  CAS  Google Scholar 

  19. Ando T, Kano D, Minakata S, Ryu N, Komatsu M (1998) Tetrahedron 54:13485

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Young researchers and elite club of IRAN (research grant). We thank Islamic Azad University for additional unrestricted support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Majid Ghazanfarpour-Darjani.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ghazanfarpour-Darjani, M., Khodakarami, A. Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines. Monatsh Chem 147, 829–835 (2016). https://doi.org/10.1007/s00706-015-1543-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1543-3

Keywords

Navigation