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Synthesis and antibacterial activities of pyrano[3,2-b]pyranones from kojic acid, ethyl cyanoacetate, and benzaldehydes in aqueous K2CO3

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Abstract

Pyrano[3,2-b]pyranones are prepared in good yields from three-component coupling of kojic acid, ethyl cyanoacetate, and benzaldehydes in aqueous K2CO3. The synthetic compounds exert moderate activity against both Gram positive and Gram negative bacteria and their effectiveness is higher against Bacillus subtilis.

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References

  1. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford, p 30

    Google Scholar 

  2. Anastas PT, Williamson T (1998) Green chemistry, frontiers in benign chemical synthesis and processes. Oxford University Press, Oxford, p 1

    Google Scholar 

  3. Varma RS (1999) Green Chem 1:43

    Article  CAS  Google Scholar 

  4. Herrerias CI, Yao X, Li Z, Li C (2007) Chem Rev 107:2546

    Article  CAS  Google Scholar 

  5. Bonifacio VDB (2005) www.organic-chemistry.org/highlights/2005/25July.shtm. Accessed 1 Oct 2013

  6. Li CJ, Chan TH (eds) (2007) Comprehensive organic reaction in aqueous media. Wiley, New Jersey, p 1

    Google Scholar 

  7. Grieco PA (1998) Organic reaction in water. Thomson Science, Glasgow

    Google Scholar 

  8. Li CJ, Chen L (2006) Chem Soc Rev 5:68

    Article  Google Scholar 

  9. Loy L, Bonsignore G, Secci D, Calignano A (1993) Eur J Med Chem 28:517

    Article  Google Scholar 

  10. Uckun FM, Chen M, Vassilev AO, Huang H, Jan ST (2000) Bioorg Med Chem Lett 10:541

    Article  CAS  Google Scholar 

  11. Gonzalez R, Martin N, Seoane C, Marco JL, Albert A, Cano FH (1992) Tetrahedron Lett 33:3809

    CAS  Google Scholar 

  12. Armesto D, Horspool WM, Martin N, Ramos A, Seaone C (1989) J Org Chem 54:3069

    Article  CAS  Google Scholar 

  13. Asghari S, Ahmadipour M (2010) Acta Chem Slov 57:953

    CAS  Google Scholar 

  14. Miya MB, Prakash Raob YJ, Krupadanam GLD (2012) Heterocycl Lett 2:214

    Google Scholar 

  15. Paul S, Bhattacharyya P, Das AR (2011) Tetrahedron Lett 52:4636

    Article  CAS  Google Scholar 

  16. Wang LM, Jiao N, Qiu J, Yu JJ, Liu JQ, Guo FL, Liu Y (2010) Tetrahedron 66:339

    Article  CAS  Google Scholar 

  17. Wang HJ, Lu J, Zhang ZH (2010) Monatsh Chem 141:1107

    Article  CAS  Google Scholar 

  18. Saeedi M, Heravi MM, Beheshtiha YS, Oskooie HA (2010) Tetrahedron 66:5345

    Article  CAS  Google Scholar 

  19. Pratap UR, Jawale DV, Netankar PD, Mane RA (2011) Tetrahedron Lett 52:5817

    Article  CAS  Google Scholar 

  20. Hilmy Elnagdi NM, Saad Al-Hokbany N (2012) Molecules 17:4300

    Article  Google Scholar 

  21. Lakshmi NV, Thirumurugan P, Noorulla KM, Perumal PT (2010) Bioorg Med Chem Lett 20:5054

    Article  CAS  Google Scholar 

  22. Khurana JM, Nand B, Saluja P (2010) Tetrahedron 66:5637

    Article  CAS  Google Scholar 

  23. Banerjee S, Horn A, Khatri H, Sereda G (2011) Tetrahedron Lett 52:1878

    Article  CAS  Google Scholar 

  24. Khan AT, Lal M, Ali S, Musawwer Khan M (2011) Tetrahedron Lett 52:5327

    Article  CAS  Google Scholar 

  25. Karami B, Khodabakhshi S, Eskandari K (2012) Tetrahedron Lett 53:1445

    Article  CAS  Google Scholar 

  26. Nagabhushana H, Sandeep Saundalkar S, Muralidhar L, Nagabhushana BM, Girija CR, Nagaraja D, Pasha MA, Jayashankara VP (2011) Chin Chem Lett 22:143

    Article  CAS  Google Scholar 

  27. Ren YM, Cai C (2008) Catal Commun 9:1017

    Article  Google Scholar 

  28. Nemouchi S, Boulcina R, Carboni B, Debache A (2012) C R Chimie 15:394

    Article  CAS  Google Scholar 

  29. Banitaba SH, Safari J, Dehghan Khalili S (2013) Ultrason Sonochem 20:401

    Article  CAS  Google Scholar 

  30. Li Y, Zhao B, Du B, Jiang Q, Wang X, Cao C (2013) Tetrahedron Lett 54:227

    Article  CAS  Google Scholar 

  31. Tenover FC (2009) Antibiotic susceptibility testing. In: Schaechter M (ed) Encyclopedia of microbiology, 3rd edn. Academic, Oxford, p 67

    Chapter  Google Scholar 

  32. Ghaemy M, Aghakhani B, Taghavi M, Nasab SMA, Mohseni M (2013) React Funct Polym 555:73

    Google Scholar 

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Acknowledgments

The authors acknowledge the University of Mazandaran for financial support of this research

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Authors and Affiliations

  1. Nano and Biotechnology Research Group, University of Mazandaran, Babolsar, Iran

    Sakineh Asghari

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, 47416-95447, Babolsar, Iran

    Sakineh Asghari, Robabeh Baharfar, Manag Alimi & Mohammad Ahmadipour

  3. Department of Biology, University of Mazandaran, Babolsar, Iran

    Mojtaba Mohseni

Authors
  1. Sakineh Asghari
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  2. Robabeh Baharfar
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  3. Manag Alimi
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  4. Mohammad Ahmadipour
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  5. Mojtaba Mohseni
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Corresponding author

Correspondence to Sakineh Asghari.

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Asghari, S., Baharfar, R., Alimi, M. et al. Synthesis and antibacterial activities of pyrano[3,2-b]pyranones from kojic acid, ethyl cyanoacetate, and benzaldehydes in aqueous K2CO3 . Monatsh Chem 145, 1337–1342 (2014). https://doi.org/10.1007/s00706-014-1190-0

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  • DOI: https://doi.org/10.1007/s00706-014-1190-0

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