Skip to main content
SpringerLink
Log in

A one-pot synthesis of functionalized ethyl 1,3-thiazole-5-carboxylates from thioamides or thioureas and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid

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

Abstract

A simple one-pot synthesis of functionalized ethyl 1,3-thiazole-5-carboxylates from the reaction of 2-chloro-1,3-dicarbonyl compounds with thioureas or thioamides in the presence of 1-butyl-3-methylimidazolium trifluoromethanesulfonate is described.

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. Breslow R (1958) J Am Chem Soc 80:3719

    Article  CAS  Google Scholar 

  2. Haviv F, Ratajczyk JD, DeNet RW, Kerdesky FA, Walters RL, Schmidt SP, Holms JH, Young PR, Carter GW (1988) J Med Chem 31:1719

    Article  CAS  Google Scholar 

  3. Patt WC, Hamilton HW, Taylor MD, Ryan MJ, Taylor DG Jr, Connolly CJC, Doherty AM, Klutchko SR, Sircar I, Steinbaugh BA, Batley BL, Painchaud CA, Rapundalo ST, Michniewicz BM, Olson SCJ (1992) J Med Chem 35:2562

    Article  CAS  Google Scholar 

  4. Tsuji K, Ishikawa H (1994) Bioorg Med Chem Lett 4:1601

    Article  CAS  Google Scholar 

  5. Bell FW, Cantrell AS, Hoegberg M, Jaskunas SR, Johansson NG, Jordon CL, Kinnick MD, Lind P, JM Morin Jr, Noreen R, Oberg B, Palkowitz JA, Parrish CA, Pranc P, Sahlberg C, Ternansky RJ, Vasileff RT, Vrang L, West SJ, Zhang H, Zhou X-X (1995) J Med Chem 38:4929

    Article  CAS  Google Scholar 

  6. Fink BA, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA (1999) Chem Biol 6:205

    Article  CAS  Google Scholar 

  7. Van Muijlwijk-Koezen JE, Timmerman H, Vollinga RC, Von Drabbe Kunzel JF, De Groote M, Visser S, Ijzerman AP (2001) J Med Chem 44:749

    Article  Google Scholar 

  8. Hantzsch A, Weber JH (1887) Ber Dtsch Chem Ges 20:3118

    Article  Google Scholar 

  9. Metzger JV (1984) Comprehensive heterocyclic chemistry. In: Katritzky R, Rees CW (eds) vol 6. Pergamon, New York, pp 235–332

  10. Welton T (1999) Chem Rev 99:2071

    Article  CAS  Google Scholar 

  11. Rogers RD, Seddon KR (eds) (2002) In ionic liquids: industrial applications to green chemistry, ACS Symposium Series 818. American Chemical Society, Washington

  12. Wasserscheid P, Welton T (eds) (2003) Ionic liquids in synthesis. Wiley-VCH, Weinheim

  13. Chiappe C (2007) Monatsh Chem 138:1035

    Article  CAS  Google Scholar 

  14. Paczal A, Kotschy A (2007) Monatsh Chem 138:1115

    Article  CAS  Google Scholar 

  15. Meindersma GW, Sa′nchez LMG, Hansmeier AR, de Haan AB (2007) Monatsh Chem 138:1125

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Science and Research Campus, Islamic Azad University, Ponak, Tehran, Iran

    Issa Yavari, S. Zahra Sayyed-Alangi & Rahimeh Hajinasiri

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

    Issa Yavari & Hadi Sajjadi-Ghotbabadi

Authors
  1. Issa Yavari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Zahra Sayyed-Alangi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rahimeh Hajinasiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hadi Sajjadi-Ghotbabadi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Issa Yavari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Sayyed-Alangi, S.Z., Hajinasiri, R. et al. A one-pot synthesis of functionalized ethyl 1,3-thiazole-5-carboxylates from thioamides or thioureas and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid. Monatsh Chem 140, 209–211 (2009). https://doi.org/10.1007/s00706-008-0065-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0065-7

Keywords

Search

Navigation