Skip to main content
SpringerLink
Log in

Regioselective synthesis of 1,3-oxathiolane-2-imine derivatives

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

Abstract

An efficient one-pot synthesis of functionalized 1,3-oxathiolane-2-imine derivatives via the reaction of aryl isothiocyanates and oxiranes is developed. This catalytic procedure takes place in the presence of MeONa in THF at 25 °C in good to excellent yields.

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

Similar content being viewed by others

References

  1. Jaramillo J, Chiara L (1994) J Org Chem 59:3135

    Article  CAS  Google Scholar 

  2. Brunel JM, Legrand O, Reymond S, Buono G (2000) Angew Chem Int Ed 39:2554

    Article  CAS  Google Scholar 

  3. Reymond S, Legrand O, Brunel JM, Buono G (2001) Eur J Org Chem 2819

  4. Zhang R, Yu WY, Lai TS, Che CM (1999) Chem Comm 409

  5. Das U, Crousse B, Kesavan V, Bonnet-Delpon D, Bégué JP (2000) J Org Chem 65:6749

    Article  CAS  Google Scholar 

  6. Reymond S, Brunel JM, Buono G (2002) Tetrahedron Asymmetry 12:3457

    Article  CAS  Google Scholar 

  7. Moghadam M, Tangestaninejad S, Mirkhani V, Shaibani R (2004) Tetrahedron 60:6105

    Article  CAS  Google Scholar 

  8. Sharghi H, Salimi Beni AR, Khalifeh R (2007) Helv Chim Acta 90:1373

    Article  CAS  Google Scholar 

  9. Naeimi H, Moradian M (2006) Can J Chem 84:1575

    Article  CAS  Google Scholar 

  10. Eshghi H, Rahimizadeh M, Shoryabi A (2005) J Iran Chem Soc 2:155

    Article  CAS  Google Scholar 

  11. Sharghi H, Nejad AH (2004) Phosphorus Sulfur Silicon Relat Elem 179:2297

    Article  CAS  Google Scholar 

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

  13. Ollevier T, Lavie-Coupin G (2004) Tetrahedron Lett 45:49

    Article  CAS  Google Scholar 

  14. Carrée F, Gil R, Collin J (2004) Tetrahedron Lett 45:7749

    Article  Google Scholar 

  15. Gil S, Torres M, Ortúzar N, Wincewicz R, Parra M (2004) Eur J Org Chem 10:2160

    Article  Google Scholar 

  16. Crotti P, Bussolo VD, Favero L, Pineschi M, Marianucci F, Renzi G, Amici G, Roselli G (2000) Tetrahedron 56:7513

    Article  CAS  Google Scholar 

  17. Arbelo DO, Prieto JA (2002) Tetrahedron Lett 43:4111

    Article  CAS  Google Scholar 

  18. Jacobsen EN, Kakiuchi F, Konsler RG, Larrow JF, Tokunaga M (1997) Tetrahedron Lett 38:773

    Article  CAS  Google Scholar 

  19. Shirayev AK, Moiseev IK, Karpeev SS (2005) Arkivoc 199

  20. Franke W, Dorfmeister G, Ganzer M, Johann G, Rees R (1990) Substituted N-phenyl-4-alkyliden-1,3-oxathiolane-2-imines, process for their preparation and their use as herbicidal agents. EP0347789, 27 Dec 1989 Chem Abstr 112:235285

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Zabol, Zabol, Iran

    Alireza Samzadeh-Kermani

Authors
  1. Alireza Samzadeh-Kermani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alireza Samzadeh-Kermani.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Samzadeh-Kermani, A. Regioselective synthesis of 1,3-oxathiolane-2-imine derivatives. Monatsh Chem 145, 611–616 (2014). https://doi.org/10.1007/s00706-013-1107-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-013-1107-3

Keywords

Search

Navigation