Advertisement

Russian Journal of General Chemistry

, Volume 86, Issue 12, pp 2900–2905 | Cite as

Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates

  • N. J. P. SubhashiniEmail author
  • M. Ravi
  • D. Cherupally
  • B. China Raju
  • E. V. Reddy
  • H. Bee
Article
  • 82 Downloads

Abstract

The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, 1H NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.

Keywords

substituted phenols 2H-chromene-3-carbaldehydes chromenyl acrylates anti-microbial activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1. (a)
    De, P., Baltas, M., and Bedos-Belval, F., Curr., Med. Chem., 2011, vol. 18, p. 1672CrossRefGoogle Scholar
  2. (b).
    Rcler, H., Dahn, K.H., Sweely, C.C., and Trost, B.M., Angew. Chem., 1967, vol. 79, p. 190. Angew. Chem., Int. Ed. Engl., 1967, vol. 6, p. 179Google Scholar
  3. (c).
    Tsuboi, T., Hatano, N., Nakatsuji, K., Fujitani, B., Yoshida, K., Shimizu, M., Kawasaki, A., Sakata, M., and Tsuboshima, M., Adv. Prostaglandin Thromboxane Res., 1980, vol. 6, p. 347PubMedGoogle Scholar
  4. (d).
    Fuller, A.T., Mellows, G., Woolford, M., Banks, G.T., Barrow, K.D., and Chain, E.B., Nature, 1971, vol. 234, p. 416CrossRefGoogle Scholar
  5. (e).
    Chain, E.B. and Mellows, G., J. Chem. Soc., Chem. Commun., 1974, p. 847. doi 10.1039/C39740000847 2.Google Scholar
  6. (a).
    Katritzky, A.R., in Comprehensive Organic Functional Group Transformations, Katritzky, A.R., Ed., Oxford: Pergamon, 1995, vol. 5, p. 154Google Scholar
  7. (b).
    Franklin, A.S., J. Chem. Soc., Perkin Trans. 1, 1998, p. 2451Google Scholar
  8. (c).
    Beletskaya, I.P. and Cheprakov, A.V., Chem. Rev., 2000, vol. 100, p. 3009CrossRefGoogle Scholar
  9. (d).
    Chatterjee, A.K., Toste, F.D., Choi, T.-L., and Grubbs, R.H., Adv. Synth. Catal., 2002, vol. 344, p. 634. doi 10.1002/1615-69(200208)344: 6/7<634::AID-ADSC634>3.0.CO;2-KCrossRefGoogle Scholar
  10. 3.
    Brunet, M., Zeiller, J.-J., Berthelon, J.-J., Contard, F., Augert, G., and Guerrier, D., US Patent Application 6596758 B1, 2003.Google Scholar
  11. 4.
    Ikeda, S., Kimura, U., Ashizawa, T., Gomi, K., and Saito, H., Japan Patent Application 08277242 A, October 22, 1996.Google Scholar
  12. 5.
    Wu, J., Wu, H., Wei, S., and Dai, W.M., Tetrahedron Lett., 2004, vol. 45, p. 4401.CrossRefGoogle Scholar
  13. 6.
    Li, A.H., Dai, L.X., and Aggarwal, V.K., Chem. Rev. 1997, vol. 97, p. 2341.CrossRefGoogle Scholar
  14. 7.
    Prajapati, D. and Sandhu, J.S., J. Chem. Soc., Perkin Trans. 1, 1993, p. 739. doi 10.1039/P19930000739Google Scholar
  15. 8.
    Varma, R.S., Kabalka, G.W., Evans, L.T., and Pagni, R.M., Synth. Commun. 1985, vol. 15, p 279.CrossRefGoogle Scholar
  16. 9.
    Zheng, M., Wang, L., Shao, J., and Zhong, Q., Synth. Commun., 1997, vol. 27, p 351.CrossRefGoogle Scholar
  17. 10.
    Sampath Kumar, H.M., Subbareddy, B.V., Anjaneyulu, S., and Yadav, J.S., Synth.Commun., 1998, vol. 28, p. 3811.CrossRefGoogle Scholar
  18. 11.
    Lin, R., Yu, Y., and Zhang, Y., Synth. Commun., 1992, vol. 23, p. 271.CrossRefGoogle Scholar
  19. 12.
    Mahrwald, R. and Schick, H., Synthesis, 1990, p. 592.Google Scholar
  20. 13.
    Gall, E.L., Texier-Boullet, F., and Hamelin, J., Synth. Commun., 1999, vol. 29, p. 3651.CrossRefGoogle Scholar
  21. 14.
    Gupta, R., Gupta, A.K., Paul, S., and Kachroo, P.L., Indian J. Chem., 1995, vol. 34, p 61.Google Scholar
  22. 15.
    Fodor, G. and Tomoskozi, I., Tetrahedron Lett., 1961, no. 2, p. 579.CrossRefGoogle Scholar
  23. 16.
    Isaacs, N.S. and El-Din, G.N., Tetrahedron Lett., 1987, vol. 28, p. 2191.CrossRefGoogle Scholar
  24. 17.
    Matikainen, J.K., Kaltia, S., and Hase, T., Synlett, 1994, p. 817.Google Scholar
  25. 18.
    Silveira, C.C., Perin, G., and Braga, A.L., J. Chem. Res., 1994, p. 492.Google Scholar
  26. 19.
    Patil, V.J. and Mävers, U., Tetrahedron Lett., 1996, vol. 37, p. 1281.CrossRefGoogle Scholar
  27. 20.
    Boulaire, V.L. and Grée, R., Chem. Commun., 2000, p. 2195.Google Scholar
  28. 21.
    El-Batta, A., Jiang, C., Zhao, W., Anness, R., Cooksy, A.L., and Bergdahl, M., J. Org. Chem., 2007, vol. 72, p. 5244.CrossRefGoogle Scholar
  29. 22.
    Dambacher, J., Zhao, W., El-Batta, A., Anness, R., Jiang, C., and Bergdahl, M., Tetrahedron Lett., 2005, vol. 46, p. 4473.CrossRefGoogle Scholar
  30. 23.
    Craig, D. and Martin, M.L., Molecules, 1998, vol. 3, p. 64.CrossRefGoogle Scholar
  31. 24.
    Laird, T., Ollis, W.D., and Sutherland, I.O., J. Chem. Soc., Perkin Trans. 1, 1980, p. 2033.Google Scholar
  32. 25.
    Piers, E. and Ruediger, E.H., J. Org. Chem., 1980, vol. 45, p. 1725.CrossRefGoogle Scholar
  33. 26.
    Legrand, S., Botton, M., Coracini, M., Witzgall, P., and Unelius, C.R., Z. Naturforsch. C, 2004, vol. 59, p. 708.CrossRefGoogle Scholar
  34. 27.
    Tomizawa, K. and Watt, D.S., Synthesis, 1985, p. 887.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • N. J. P. Subhashini
    • 1
    Email author
  • M. Ravi
    • 1
  • D. Cherupally
    • 2
  • B. China Raju
    • 2
  • E. V. Reddy
    • 2
  • H. Bee
    • 3
  1. 1.Department of Pharmacy, University College of TechnologyOsmania UniversityHyderabadIndia
  2. 2.Natural Products Chemistry DivisionCSIR Indian Institute of Chemical TechnologyTarnakaIndia
  3. 3.Department of Microbiology, University College of ScienceOsmania UniversityHyderabadIndia

Personalised recommendations