1887
Volume 2013, Issue 1
  • EISSN: 2223-506X

Abstract

Attempts to produce greener bromination of 2-acetyl 9-fluorene with KBr+KBrO reagent using fly-ash:HO catalyst in aqueous media gave 9H-fluorenacylbromides. Generally, the halo-keto compounds possess insect antifeedant activities. Therefore, the insect antifeedant activities of these acyl bromides have been studied using 4th instar larvae against castor semilooper. Solvent free bromination method was used for synthesizing some 9H-fluorenacylbromides. They were characterized by UV, IR, NMR and mass spectroscopic data. Castor-leaf discs were used for evaluation of insect antifeedant activities of the synthesized acyl bromides. The yields of synthesized acyl bromides were over 60%. The physical constants, analytical and spectral data of these ketones has been determined. Halo substituted acyl bromides gave good insect antifeedant activities. Easy handling, non-hazardous and environmentally benign bromination methods have been adopted for synthesizing acyl bromides with good yields. Bromo substituted acyl bromides show better insect antifeedant activity.

Loading

Article metrics loading...

/content/journals/10.5339/connect.2013.6
2013-07-01
2024-04-24
Loading full text...

Full text loading...

/deliver/fulltext/connect/2013/1/connect.2013.6.html?itemId=/content/journals/10.5339/connect.2013.6&mimeType=html&fmt=ahah

References

  1. Thirunarayanan G, Gopalakrishnan M, Vanangamudi G, Spectrochim Acta. 2007; 67A::1106
    [Google Scholar]
  2. Thirunarayanan G, Vanangamudi G, Sathiyendiran V, Ravi K, Indian J Chem. 2011; 50B::593
    [Google Scholar]
  3. Lou JD, Xu ZN, Tetrahedron Lett. 2002; 43:35:6149
    [Google Scholar]
  4. Cave GW, Hardie MJ, Roberts BA, Raston CL, Eur J Org Chem. 2001;:3227
    [Google Scholar]
  5. Kalluraya B, Ray G, Indian J Chem. 2003; 42:B:2556
    [Google Scholar]
  6. Thirunarayanan G, Vanangamudi G, Arkivoc. 2006; 12::58
    [Google Scholar]
  7. Bamoharram FF, Heravi MM, Roshani M, Jahangir M, Gharib A, J Mol Catal. 2007; 271A:1–2:126
    [Google Scholar]
  8. Adimurthy S, Ramachandraiah G, Bedekar AV, Ghosh S, Ranu BC, Gosh PK, Green Chem. 2006; 8::916
    [Google Scholar]
  9. Sharghi H, Hosseini Sarvari M, Tetrahedron. 2003; 59:20:3627
    [Google Scholar]
  10. Paul BD, Dreka C, Summers JL, Smith ML, J Anal Toxicol. 1996; 20:6:506
    [Google Scholar]
  11. Deli J, Loand T, Foldsi D, Pharmazie. 1984; 39:8:539
    [Google Scholar]
  12. Wu LQ, Yang CG, Wu YF, Yang LM, J Chin Chem Soc. 2009; 56:3:606
    [Google Scholar]
  13. King LC, Ostrum GK, J Org Chem. 1964; 29:12:3459
    [Google Scholar]
  14. Levene PA, Org Synth. 1943; II::88
    [Google Scholar]
  15. Pearson DE, Pope HW, Hargrove WW, Org Synth. 1973; II::117
    [Google Scholar]
  16. In: Fieser LFFiese M, eds.Reagents for Organic Synthesis. Vol.1. Wiley-India; 1971:p.334
    [Google Scholar]
  17. Paul S, Gupta V, Gupta R, Loupy A, Tetrahedron Lett. 2003; 44:3:439
    [Google Scholar]
  18. Sanches EI, Fumarola MJ, J Org Chem. 1982; 47:8:1588
    [Google Scholar]
  19. Kajigaeshi S, Kakinami T, Okamoto T, Fujisaki S, Bull Chem. Soc, Jpn. 1987; 60:3:1159
    [Google Scholar]
  20. Bora U, Dey D, Dhar S, Chaudhuri MK, Pure Appl Chem. 2001; 73::93
    [Google Scholar]
  21. Mayeno AN, Curran AJ, Roberts RL, Foote CS, J Biol Chem. 1989; 264:10:5660
    [Google Scholar]
  22. Chaudhuri MK, Khan AT, Patel BK, Dey D, Kharmawphlang W, Lakshmiprapha TR, Mandal GC, Tetrahedron Lett. 1998; 39:44:8163
    [Google Scholar]
  23. Cajetan DI, Bekele T, France S, Wolfer J, Weatherwax A, Taggi AE, Lectka T, J Org Chem. 2006; 71::8946
    [Google Scholar]
  24. Lovins RE, Anrews LJ, Keef RW, J Org Chem. 1963; 28::2847
    [Google Scholar]
  25. Starostenko NE, Adeeva NO, Zeiberlikh FN, Kurkovskaya LN, Suvorov NN, Chem Heterocycl Compds. 1987; 23::271
    [Google Scholar]
  26. Kumar L, Sharma V, Mahajan T, Agarwal DD, Org Process Res Dev. 2010; 14::174
    [Google Scholar]
  27. Patwari SB, Baseer MA, Vibhute YB, Bhusare SR, Tetrahedron Lett. 2003; 44:26:4893
    [Google Scholar]
  28. Thirunarayanan G, J Indian Chem Soc. 2008; 85:4:447
    [Google Scholar]
  29. Thirunarayanan G, Surya S, Srinivasan S, Vanangamudi G, Sathiyendiran V, Spectrochim Acta. 2010; 75A::152156
    [Google Scholar]
  30. Thirunarayanan G, Vanangamudi G, Spectrochim Acta. 2011; 81A::390
    [Google Scholar]
  31. Dethler VG. Chemical Insect Attractants and Repellents. Philadelphia: Blackistan 1947;:210
    [Google Scholar]
  32. Thirunarayanan G, Iup J, Iup J Chem. 2010; 3:4:35
    [Google Scholar]
  33. Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, Govindaraju R, Arkivoc. 2006; 13::130
    [Google Scholar]
  34. Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, J Korean Chem Soc. 2007; 51:6:520
    [Google Scholar]
  35. Thirunarayanan G, Vanangamudi G, Subramanian M, Elixir Org Chem. 2012; 43::6987
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journals/10.5339/connect.2013.6
Loading
/content/journals/10.5339/connect.2013.6
Loading

Data & Media loading...

  • Article Type: Research Article
Keyword(s): 9H-fluorenacyl bromidesfly-ash:H2OInfrared spectraInsect antifeedant activity and NMR spectra
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error