Skip to main content
SpringerLink
Log in

Heteropolyacid catalyzed formation of thioparabanic acid derivatives

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

Abstract

A heteropoly acid-catalyzed reaction between amines, ammonium thiocyanate, and oxalate esters is reported. This route turned out to be a useful method for the preparation of thioparabanic acid derivatives.

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

Fig. 1

Similar content being viewed by others

References

  1. Ward SE, Harrington FP, Gordon LJ, Hopley SC, Scott CM, Watson JM (2005) J Med Chem 48:3478

    Article  CAS  Google Scholar 

  2. Massari S, Daelemans D, Barreca ML, Knezevich A, Sabatini S, Cecchetti V, Marcello A, Pannecouque C, Tabarrini O (2010) J Med Chem 53:641

    Article  CAS  Google Scholar 

  3. Soneda T, Takeshita H, Kagoshima Y, Yamamoto Y, Hosokawa T, Konosu T, Masuda N, Uchida T, Achiwa I, Kuroyanagi J, Fujisawa T, Yokomizo A, Noguchi T (2009) Preparation of imidazolecarboxamide derivatives as antibacterial agents. Chem Abstr 151:148320 (WO 2009084614, Jul 9, 2009)

    Google Scholar 

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

    Article  Google Scholar 

  5. Tu SJ, Zhang XH, Han ZG, Cao XD, Wu SS, Yan S, Hao WJ, Zhang G, Ma N (2009) J Comb Chem 11:428

    Article  CAS  Google Scholar 

  6. Evdokimov NM, Kireev AS, Yakovenko AA, Antipin MY, Magedov IV, Kornienko A (2007) J Org Chem 72:3443

    Article  CAS  Google Scholar 

  7. Allais C, Grassot JM, Rodriguez J, Constantieux T (2014) Chem Rev 114:10829

    Article  CAS  Google Scholar 

  8. Yavari I, Ghazanfarpour-Darjani M, Sabbaghan M, Hossaini Z (2007) Tetrahedron Lett 48:3749

    Article  CAS  Google Scholar 

  9. Ghazanfarpour-Darjani M, Babapour-Kooshalshahi M, Mousavi-Safavi SM, Akbari J, Khalaj M (2015) Synlett 27:259

    Article  Google Scholar 

  10. Ma D, Lu X, Shi L, Zhang H, Jiang Y, Liu X (2011) Angew Chem Int Ed 50:1118

    Article  CAS  Google Scholar 

  11. Yavari I, Ghazanfarpour-Darjani M, Nematpour M (2015) Tetrahedron Lett 56:2416

    Article  CAS  Google Scholar 

  12. Yavari I, Ghazanfarpour-Darjani M, Bayat MJ, Malekafzali A (2014) Synlett 25:959

    Article  CAS  Google Scholar 

  13. Heravi MM, Sadjadi S (2009) J Iran Chem Soc 6:1

    Article  CAS  Google Scholar 

  14. Kozhevnikov IV (1998) Chem Rev 98:171

    Article  CAS  Google Scholar 

  15. Gulliya KS, Franck B, Schneider U, Sharma R, Arnold L, Matthews JL (1994) Photooxidation products and derivatives thereof of merocyanine-540, their preparation and uses as anticancer and antiviral agents. Chem Abstr 121:108825 (US Patent 5,312,919, May 17, 1994)

    Google Scholar 

  16. Gulliya KS, Sharam R, Liu HW, Arnold L, Matthews JL (1995) Anticancer Drugs 6:545

    Article  CAS  Google Scholar 

  17. Kotani T, Nagaki Y, Ishii A, Konishi Y, Yago H, Suehiro S, Okukado N, Okamoto K (1997) J Med Chem 40:684

    Article  CAS  Google Scholar 

  18. Butera JA, Elokdah HM, Sulkowski TS, Primeau JL, Lennox JR, Graceffa RF (2006) Preparation of 1,3-disubstituted-2-thioxoimidazolidine-4,5-diones as potassium channel openers. Chem Abstr 139:69265 (US Patent 7,115,620, October 3, 2006; (2003))

    Google Scholar 

  19. Sunduru N, Srivastava K, Rajakumar S, Puri SK, Saxena JK, Chauhan PM (2009) Bioorg Med Chem Lett 19:2570

    Article  CAS  Google Scholar 

  20. Elokdah H, Sulkowski TS, Gharbia MA, Butera JA, Chai SY, Mcfarlane GR, Mckean ML, Babiak JL, Adelman SJ, Quine EM (2004) J Med Chem 47:681

    Article  CAS  Google Scholar 

  21. Fahmy HH, Soliman GA (2001) Arch Pharm Res 24:180

    Article  CAS  Google Scholar 

  22. Elokdah H, Sulkowski TS (2003) Preparation of 1,3-disubstituted-2-thioxoimidazolidine-4,5-diones for the treatment of atherosclerosis. Chem Abstr 139:69264 (US Patent 20030119889, Jun 26, 2003)

    Google Scholar 

  23. Schmeyers J, Kaupp G (2002) Tetrahedron 58:7241

    Article  CAS  Google Scholar 

  24. Aragoni MC, Arca M, Devillanova FA, Hursthouse MB, Huth SL, Isaia F, Lippolis V, Mancini A, Ogilvie HR, Verani G (2005) J Organomet Chem 690:1923

    Article  CAS  Google Scholar 

  25. Yavari I, Souri S, Sirouspour M (2008) Synlett 19:1633

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  27. Samzadeh-Kermani A (2014) Synlett 25:1839

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. Samzadeh-Kermani A (2016) Monatsh Chem 147:761

    Article  CAS  Google Scholar 

  30. Bardin BB, Bordawekar SV, Neurock M, Davis RJ (1998) J Phys Chem B 102:10819

    Article  Google Scholar 

  31. Tsigdinos GA, Hallada C (1968) J Inorg Chem 7:437

    Article  CAS  Google Scholar 

  32. Izumi Y, Hasebe R, Urabe K (1983) J Catal 84:402

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Generous financial support from the Zabol University of Iran is gratefully acknowledged.

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.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3769 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. Heteropolyacid catalyzed formation of thioparabanic acid derivatives. Monatsh Chem 148, 339–345 (2017). https://doi.org/10.1007/s00706-016-1774-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1774-y

Keywords

Search

Navigation