Skip to main content
SpringerLink
Log in

A synthesis of functionalized 2-imino-1,3-thiazoles from tetramethylguanidine, isothiocyanates, and 2-chloro-1,3-dicarbonyl compounds

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

The Hantzsch method for thiazole synthesis is modified via the reaction of 2-chloro-1,3-dicarbonyl compounds with 2-(amidosulfanylenemethyl)-1,1,3,3-tetramethylguanidines (prepared in situ from tetramethylguanidine and isothiocyanates), to afford functionalized 2-imino-1,3-thiazoles in good 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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. I. Ugi, A. Dömling, Endeavour 18, 115 (1994)

    Article  CAS  Google Scholar 

  2. S. Heck, A. Dömling, Synlett 424 (2000)

  3. T. Ziegler, H.J. Kaiser, R. Schlomer, C. Koch, Tetrahedron 55, 8397 (1999)

    Article  CAS  Google Scholar 

  4. J.M. Lehn, in Supramolecular Chemistry-Concepts and Perspectives, Ch. 8 (VCH, Weinheim, 1995)

  5. T. Jorgensen, T.K. Hansen, J. Becer, Chem. Soc. Rev. 23, 41 (1994)

    Article  CAS  Google Scholar 

  6. J.V. Metzger, in Thiazole and its Derivatives, (Wiley & Sons, New York, 1979)

  7. A.A. Kiryanov, P. Sampson, A.J. Seed, J. Org. Chem. 66, 7925 (2001)

    Article  CAS  Google Scholar 

  8. T. Bach, S. Heuser, Tetrahedron Lett. 41, 1707 (2000)

    Article  CAS  Google Scholar 

  9. D. Shin, J. Lee, H.G. Hahn, Tetrahedron 66, 5707 (2010)

    Article  CAS  Google Scholar 

  10. D.S. Millan, R.H. Prager, C. Brand, P.H. Hart, Tetrahedron 56, 811 (2000)

    Article  CAS  Google Scholar 

  11. W.L. Wang, D.Y. Yao, M. Gu, M.Z. Fan, J.W. Li, Y.C. Xing, F.J. Nan, Bioorg. Med. Chem. Lett. 15, 5284 (2005)

    Article  CAS  Google Scholar 

  12. R.H. Wiley, D.C. England, L.C. Behr, In Organic Reactions, vol. 6 (Wiley & Sons, New York, 1951) p. 367

  13. I. Yavari, S. Beheshti, J. Iran. Chem. Soc. 8, 1030 (2011)

    Article  CAS  Google Scholar 

  14. I. Yavari, A. Aminkhani, S. Skoulika, J. Iran. Chem. Soc. 9, 0000 (2012)

    Google Scholar 

  15. I. Yavari, A.S. Shahvelayati, A. Malekafzali, J. Sulfur Chem. 31, 499 (2010)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

    Issa Yavari, Alaleh Malekafzali & Samereh Seyfi

Authors
  1. Issa Yavari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alaleh Malekafzali
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samereh Seyfi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Issa Yavari.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1771 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Malekafzali, A. & Seyfi, S. A synthesis of functionalized 2-imino-1,3-thiazoles from tetramethylguanidine, isothiocyanates, and 2-chloro-1,3-dicarbonyl compounds. J IRAN CHEM SOC 11, 285–288 (2014). https://doi.org/10.1007/s13738-013-0299-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-013-0299-0

Keywords

Search

Navigation