Skip to main content
SpringerLink
Log in

Palladium-catalyzed arylations in 4-pyrone systems: 2,6-diaryl-3,5-dibromo-4-pyrones and kojic acid

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

Abstract

Palladium-catalyzed cross-coupling reactions of 2,6-diaryl-3,5-dibromo-4-pyrones with imidazole and benzimidazole in the presence of N,N′-dibutylbenzimidazol-2-ylidene as ligand resulted in the formation of the monosubstituted C- and N-arylated products. Kojic acid was also treated with some aryl halides at the same conditions, to afford C-6 arylated 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
Fig. 2

Similar content being viewed by others

References

  1. Wu Y, Wang J, Mao F, Kwong FY (2014) Chem Asian J 9:26

    Article  CAS  Google Scholar 

  2. Wu XF, Neumann H, Beller M (2013) Chem Rev 113:1

    Article  Google Scholar 

  3. Yokoyama H, Kubo T, Matsumura Y, Hosokawa J, Miyazawa M, Hirai Y (2013) Tetrahedron 70:9530

    Article  Google Scholar 

  4. Wencel-Delord J, Glorius F (2013) Nat Chem 5:369

    Article  CAS  Google Scholar 

  5. Sun CL, Li H, Yu DG, Yu M, Zhou X, Lu XY, Huang K, Zheng SF, Li BJ, Shi ZJ (2010) Nat Chem 2:1044

    Article  CAS  Google Scholar 

  6. Wang GW, Yuan TT, Li DD (2011) Angew Chem Int Ed 50:1380

    Article  CAS  Google Scholar 

  7. Subba Reddy BV, Ramesh K, Yadav JS (2011) Synlett 2:169

  8. René O, Fagnou K (2010) Org Lett 12:2116

    Article  Google Scholar 

  9. Eastman K, Baran PS (2009) Tetrahedron 65:3149

    Article  CAS  Google Scholar 

  10. Valente C, Çalimsiz S, Hoi KH, Mallik D, Sayah M, Organ MG (2012) Angew Chem Int Ed 51:3314

    Article  CAS  Google Scholar 

  11. Ozdemir I, Gök Y, Özeroğlu Ö, Kaloğlu M, Doucet H, Bruneau C (2010) Eur J Inorg Chem 12:1798

    Article  Google Scholar 

  12. Viciu MS, Germaneau RF, Navarro-Fernandez O, Stevens ED, Nolan SP (2002) Organometallics 21:5470

    Article  CAS  Google Scholar 

  13. Doǧan Ö, Demir S, Özdemir I, Çetinkaya B (2011) Appl Organomet Chem 25:163

    Article  Google Scholar 

  14. Haque RA, Iqbal MA, Budagumpi S, Ahamed MBK, Abdul Majid AMS, Hasanudin N (2013) Appl Organomet Chem 27:214

  15. Xu H, Liu WQ, Fan LL, Chen Y, Yang LM, Lv L, Zheng YT (2008) Chem Pharm Bull 56:720

    Article  CAS  Google Scholar 

  16. Xiao L, Chen Z, Qu B, Luo J, Kong S, Gong Q, Kido J (2011) Adv Mater 23:926

    Article  CAS  Google Scholar 

  17. Chen H, Hong F, Shao G, Hang D, Zhao L, Zeng Z (2014) Chem Asian J 9:3418

    Article  CAS  Google Scholar 

  18. Bolm C, Hildebrand JP, Muñiz K, Hermanns N (2001) Angew Chem Int Ed 40:3284

    Article  CAS  Google Scholar 

  19. Neupane P, Xia L, Lee YR (2014) Adv Synth Catal 356:2566

    Article  CAS  Google Scholar 

  20. Kamino T, Kuramochi K, Kobayashi S (2003) Tetrahedron Lett 44:7349

    Article  CAS  Google Scholar 

  21. South MS, Ma CC, Koeller KJ, Rahman HK, Neumann WL (2005) Preparation of polycyclic aryl and heteroaryl substituted 4-pyrones useful for selective inhibition of the coagulation cascade. US Patent 6,916,847 B2, Jul 12, 2005; (2001) Chem Abstr 135:303776

  22. Caturla F, Amat M, Reinoso RF, Calaf E (2006) Bioorg Med Chem Lett 16:3605

    Article  CAS  Google Scholar 

  23. Liu X, Xia W, Jiang Q, Xu Y, Yu P (2014) J Agric Food Chem 62:297

    Article  CAS  Google Scholar 

  24. Sharma DK, Pandey J, Tamrakar AK, Mukherjee D (2014) Eur J Med Chem 85:727

    Article  CAS  Google Scholar 

  25. Li Y, Jiang Q, Wang K, Du B, Wang X (2013) Tetrahedron Lett 54:7147

    Article  CAS  Google Scholar 

  26. Shahrisa A, Ghasemi Z, Saraei M (2009) J Heterocycl Chem 46:273

    Article  CAS  Google Scholar 

  27. Ghasemi Z, Kalantar-Esfangare H (2015) Heterocycl Commun 21:37

    CAS  Google Scholar 

  28. Zhang Y, Ni G, Li C, Xu S, Zhang Z, Xie X (2015) Tetrahedron 71:4927

    Article  CAS  Google Scholar 

  29. Ghasemi Z, Nazari-Belvirdi V, Allahvirdinasab M, Shahrisa A (2011) Heterocycles 83:117

    Article  CAS  Google Scholar 

  30. Nawwar GAM, Grant NM, Swellem RH, Elseginy SAM (2013) Der Pharm Chem 5:241

    CAS  Google Scholar 

  31. Chawla A, Sharma A, Sharma AK (2012) Der Pharm Chem 4:116

    CAS  Google Scholar 

  32. Bellina F, Calandri C, Cauteruccio S, Rossi R (2007) Tetrahedron 63:1970

    Article  CAS  Google Scholar 

  33. Anderson KW, Tundel RE, Ikawa T, Altman RA, Buchwald SL (2006) Angew Chem Int Ed 45:6523

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to Research Affair of the University of Tabriz for financial support.

Author information

Authors and Affiliations

  1. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, 5166614766, Tabriz, Iran

    Zarrin Ghasemi, Fatemeh Poorhossain Mejarshin, Zahra Fathi & Aziz Shahrisa

Authors
  1. Zarrin Ghasemi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fatemeh Poorhossain Mejarshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zahra Fathi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Aziz Shahrisa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aziz Shahrisa.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2961 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ghasemi, Z., Poorhossain Mejarshin, F., Fathi, Z. et al. Palladium-catalyzed arylations in 4-pyrone systems: 2,6-diaryl-3,5-dibromo-4-pyrones and kojic acid. Monatsh Chem 147, 1107–1111 (2016). https://doi.org/10.1007/s00706-015-1589-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1589-2

Keywords

Search

Navigation