Skip to main content
Log in

Isocyanide-based multicomponent reaction for the formation of 1,3-oxathiolane-2-imine derivatives

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

Abstract

The adduct of isocyanide and elemental sulfur has been employed as the isothiocyanate source in reaction with oxirane to form 1,3-oxathiolane-2-imine derivatives. The optimum conditions are developed using HMPA at 55 °C for 12 h. Various isocyanides and oxiranes were tolerated under the optimum 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. Chemler SR, Fuller PH (2007) Chem Soc Rev 36:1153

    Article  CAS  Google Scholar 

  2. Robbins DW, Hartwig JF (2011) Science 333:1423

    Article  CAS  Google Scholar 

  3. Nakamura I, Yamamoto Y (2004) Chem Rev 104:2127

    Article  CAS  Google Scholar 

  4. Carsona CA, Kerr MA (2009) Chem Soc Rev 38:3051

    Article  Google Scholar 

  5. McMurray L, O’Haraa F, Gaunt MJ (2011) Chem Soc Rev 40:1885

    Article  CAS  Google Scholar 

  6. Lee HM, Nieto-Oberhuber C, Shair MD (2008) J Am Chem Soc 130:16864

    Article  CAS  Google Scholar 

  7. Dondoni A, Massi A (2006) Acc Chem Res 39:451

    Article  CAS  Google Scholar 

  8. D’Souzaa DM, Müller TJJ (2007) Chem Soc Rev 36:1095

    Article  Google Scholar 

  9. Hoppe D, Schollkopf U (1972) Liebigs Ann Chem 763:1

    Article  CAS  Google Scholar 

  10. Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L (2003) Acc Chem Res 36:899

    Article  CAS  Google Scholar 

  11. Dömling A (2006) Chem Rev 106:17

    Article  Google Scholar 

  12. Peng J, Gao Y, Hu W, Gao Y, Hu M, Wu W, Ren Y, Jiang H (2016) Org Lett 18:5924

    Article  CAS  Google Scholar 

  13. Kroon E, Kurpiewska K, Kalinowska-Tłuścik J, Dömling A (2016) Org Lett 18:4762

    Article  CAS  Google Scholar 

  14. Zheng D, Liu T, Liu X, Fan X, Wu J (2016) J Org Chem 81:9428

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  16. Ghazanfarpour-Darjani M, Khodakarami A (2016) Monatsh Chem 147:829

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. Yavari I, Ghazanfarpour-Darjani M, Solgi Y, Ahmadian S (2011) Helv Chim Acta 94:639

    Article  CAS  Google Scholar 

  20. Jing-Yu W, Zhi-Bin L, Li-Xin D, Xue-Long H (2008) J Org Chem 73:9137

    Article  Google Scholar 

  21. Samzadeh-Kermani A (2015) Synlett 26:643

    Article  CAS  Google Scholar 

  22. Ghazanfarpour-Darjani M, Babapour-Kooshalshahi M, Mousavi-Safavi SM, Akbari J, Khalaj M (2016) Synlett 27:259

    Article  CAS  Google Scholar 

  23. Khalaj M, Ghazanfarpour-Darjani M (2016) Monatsh Chem 147:2043

    Article  CAS  Google Scholar 

  24. Samzadeh-Kermani A (2016) Tetrahedron 72:5301

    Article  CAS  Google Scholar 

  25. Samzadeh-Kermani A (2016) SynthLett 27:2213.

    CAS  Google Scholar 

  26. Samzadeh-Kermani A (2017) Monatsh Chem 148:339

    Article  CAS  Google Scholar 

  27. Samzadeh-Kermani A (2016) SynthLett 27:461.

    CAS  Google Scholar 

  28. Boyer JH, Ramakrishnan VT (1972) J Org Chem 37:1360

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alireza Samzadeh-Kermani.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 4499 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Samzadeh-Kermani, A., Zamenraz, S. Isocyanide-based multicomponent reaction for the formation of 1,3-oxathiolane-2-imine derivatives. Monatsh Chem 148, 1753–1760 (2017). https://doi.org/10.1007/s00706-017-1939-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-1939-3

Keywords

Navigation