Skip to main content
Log in

Microwave-assisted synthesis of 10-aryl-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehydes by Suzuki coupling and their antimicrobial activity

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A series of new pyranochromenes has been synthesized by conventional and microwave irradiation methods from 10-chloro-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehyde using the Suzuki coupling. All the synthesized compounds were characterized by standard spectroscopic methods and elemental analysis and screened for their antibacterial and antifungal activities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1

Similar content being viewed by others

References

  1. Hermakens, P. H.; Ottenheijm, H. C.; Rees, D. C. Tetrahedron 1997, 53, 5643.

    Article  Google Scholar 

  2. Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Nicolaides, D. N. Curr. Pharm. Des. 2004, 10, 3813.

    Article  CAS  Google Scholar 

  3. Mulwad, V. V.; Shirodkhar, J. M. Indian J. Heterocycl. Chem. 2002, 11, 192.

    Google Scholar 

  4. Manohar, K.; Manjunath, G.; Raviraj, K. Indian J. Heterocycl. Chem. 2004, 13, 201.

    Google Scholar 

  5. Rajeshwar Rao, V.; Srimanth, K.; Vijaya Kumar, P. Indian J. Heterocycl. Chem. 2004, 14, 141.

    Google Scholar 

  6. Nofal, Z. M.; El-Zahar, M. I.; Abd El-Karim, S. S. J. Antimicrob. Agents Chemother. 2005, 5, 483.

    Google Scholar 

  7. Karia, D. C.; Pandya, H. K.; Godvani, N. K. Asian J. Biochem. Pharm. Res. 2012, 2(2), 126.

    CAS  Google Scholar 

  8. Thereja, S.; Verma, A.; Kalra, A.; Gosain, S.; Rewatkar, P. V.; Kokil, G. R. Acta Pol. Pharm. 2010, 67, 423.

    Google Scholar 

  9. Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Cancer Res. 1975, 35, 4750.

    Google Scholar 

  10. Mori, J.; Iwashima, M.; Takeuchi, M.; Saito, H. Chem. Pharm. Bull. 2006, 54, 391.

    Article  CAS  Google Scholar 

  11. Sandeep, G.; Sri Ranganath, Y.; Bhasker, S.; Rajkumar, N. Asian J. Res. Chem. 2009, 2, 46.

    CAS  Google Scholar 

  12. Thomas, N.; Zachariah, S. M. Asian J. Pharm. Clin. Res. 2013, 6(Suppl. 2).

  13. Cohen, A. J. Food Cosmet. Toxicol. 1979, 17, 277.

    Article  CAS  Google Scholar 

  14. Nishino, H.; Okuyama, T.; Takata, M.; Shibata, S.; Tokuda, H.; Takayasu, J.; Hasegawa, T.; Nishino, A.; Ueyama, H.; Iwashima, A. Carcinogenesis 1990, 11, 1557.

    Article  CAS  Google Scholar 

  15. Xu, Z. Q.; Flavin, M. T., Jenta, T. R. Curr. Opin. Drug Discovery Dev. 2000, 3, 155.

    CAS  Google Scholar 

  16. Laure, F; Raharivelomanana, P; Butaud, J. F.; Bianchini, J. P.; Gaydou, E. M. Anal Chim Acta. 2008, 624, 147.

    Article  CAS  Google Scholar 

  17. McKee, T. C.; Fuller, R. W.; Covington, C. D.; Cardellina, J. H., II; Gulakowski R. J.; Krepps, B. L.; McMahon, J. B.; Boyd, M. R. J. Nat. Prod. 1996, 59, 754.

    Article  CAS  Google Scholar 

  18. Littke, A. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VHC: Weinheim, 2009, p. 25.

    Chapter  Google Scholar 

  19. Suzuki, A. In Boronic Acids. Preparation, Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VHC: Weinheim, 2005, p. 123.

    Google Scholar 

  20. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047.

    Article  CAS  Google Scholar 

  21. (a) Gedye, R. N.; Wei, J. B. Can. J. Chem. 1998, 76, 525. (b) Varma, R. S. Green Chem. 1999, 1, 43.

  22. Ashok, D.; Ganesh, A. Indian J. Heterocycl. Chem. 2014, 24, 7.

    Google Scholar 

  23. Ashok, D.; Sudershan, K.; Khalilullah, M. Green Chem. Lett. Rev. 2012, 5, 121.

    Article  CAS  Google Scholar 

  24. Ashok, D.; Shravani, D. Tetrahedron Lett. 2008, 49, 7227.

    Article  CAS  Google Scholar 

  25. Ashok, D.; Sudershan, K.; Khalilullah, M. Indian J. Heterocycl. Chem. 2012, 21, 401.

    Google Scholar 

  26. Ashok, D.; Vijaya Lakshmi, B.; Arram Ganesh; Ravi, S.; Adam S.; Murthy, S. D. S. Russ. J. Gen. Chem. 2014, 84, 2234.

  27. Anderson, S. C.; Handy, S. T. Synthesis 2010, 2721.

  28. Benson, H. J. Microbiological Applications; 5th ed.; Boston: W. C. Brown Publications, 1990, p. 134.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dongamanti Ashok.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(5), 462–466

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 1654 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ashok, D., Lakshmi, B.V., Ravi, S. et al. Microwave-assisted synthesis of 10-aryl-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehydes by Suzuki coupling and their antimicrobial activity. Chem Heterocycl Comp 51, 462–466 (2015). https://doi.org/10.1007/s10593-015-1719-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1719-0

Keywords

Navigation