Skip to main content
Log in

Basic resin mediated efficient one-pot synthesis of carbazates from the corresponding alkyl halides

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A quick and efficient, one-pot synthesis of carbazates was accomplished in high yields by the reaction of various primary, secondary, and tertiary alkyl halides with a variety of substituted hydrazines using Amberlite IRA 400 basic resin/CO2 system. The reaction conditions were mild with simpler work-up procedures than the previously reported methods.

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.

Similar content being viewed by others

References

  1. U. Ragnarsson, Chem. Soc. Rev. 30 (2001) 205

    CAS  Google Scholar 

  2. E.U. Schmidt, Hydrazine and its Derivatives Preparation, Properties, Applications, 2nd ed., Wiley- Interscience, New York, 2001.

    Google Scholar 

  3. M.S.C. Pedras, M. Jha, Bioorg. Med. Chem. 14 (2006) 4958

    CAS  Google Scholar 

  4. Shailendra, N. Bharti, F. Naqvi, A. Azam, Helv. Chim. Acta 85 (2002) 2713

    CAS  Google Scholar 

  5. N. Bharti, M.R. Maurya, F. Naqvi, A. Azam, Bioorg. Med. Chem. Lett. 10 (2000) 2243

    CAS  Google Scholar 

  6. N. Bharti, M.R. Mannar, N. Fehmida, A. Bhattacharya, S. Bhattacharya, A. Azam, Eur. J. Med. Chem. 35 (2000) 481.

    Google Scholar 

  7. S.K. Sengupta, O.P. Pandey, P.G. Rao, Sugarcane Pathology 1 (1999) 279

    CAS  Google Scholar 

  8. H.S. Chen, Z.H. Li, Y.H. Han, Z.W. Wang Chin. Chem. Lett. 10 (1999) 365

    Google Scholar 

  9. K. Chaturvedi, A.K. Jaiswal, K.N. Mishra, O.P. Pandey, S.K. Sengupta, ACH-Models in Chemistry 135 (1998) 93

    CAS  Google Scholar 

  10. G.C. Briggs, C.L. Cornell, D.J. Mansfield, R.M. Turner, PCT Int Appl. 1999, WO9923066, CAN:130:337920 (1999).

    Google Scholar 

  11. T.J. Connolly, A.J. Crittal, A.S. Ebrahim, G. Ji, Org. Process. Res. Dev. 4 (2000) 526

    CAS  Google Scholar 

  12. M.S. Gordan, J.G. Krause, M.A. Linneman-Mohr, R.R. Parchue, Synthesis 3 (1998) 244

    Google Scholar 

  13. M.J. Hauser, J. Org. Chem. 31 (1966) 968.

    CAS  Google Scholar 

  14. S. Sakakibara, I. Honda, M. Naruse, M. Kanaoka, Experimentia 25 (1969) 576

    CAS  Google Scholar 

  15. S. Sakakibara, I. Honda, K. Takada, M. Miyoshi, T. Ohnishi, K. Okumura Bull. Chem. Soc. Jpn. 42 (1969) 809

    Google Scholar 

  16. M. Quibell, W.G. Turnell, T. Johnson, J. Chem. Soc. Perkin. Trans. I 22 (1993) 2843

    Google Scholar 

  17. C.J. Gray, M. Quibell, N. Baggett, T. Hammerle, Int. J. Pept. Protien Res. 40 (1992) 351.

    CAS  Google Scholar 

  18. J.Y. Huang, H.S. Choi, D.H. Lee, S.E. Yoo, Y.D. Gong, J. Comb. Chem. 7 (2005) 136

    Google Scholar 

  19. J.Y. Hwang, H. S. Choi, D.H. Lee, Y.D. Gong, J. Comb. Chem. 7 (2005) 816.

    CAS  Google Scholar 

  20. C. Bolzati, E. Benini, M. Cavazza-Ceccato, E. Cozzala, E. Malago, S. Agostini, F. Tisato, F. Rofosco, G. Bandoli, Bioconjugate Chemistry 17 (2006) 419

    CAS  Google Scholar 

  21. M.A. Ali, A.H. Mirza, R.J. Butcher, K.A. Krause, Transit. Metal Chem. 31 (2006) 79

    CAS  Google Scholar 

  22. R. Singh, N.K. Kaushik, Main Group Met. Chem. 27 (2004) 327.

    CAS  Google Scholar 

  23. H. Dyker, J. Scherkenbeck, D. Gondol, A. Goehrt, A. Harder, J. Org. Chem. 66 (2001) 3760.

    CAS  Google Scholar 

  24. A.S. Dutta, J.S. Morley, J. Chem. Soc. Perkin Trans. I 1712 (1975)

    Google Scholar 

  25. S. Nara, T. Sakamoto, E. Miyazawa, Y. Kikugawa, Synth. Commun. 33 (2003) 87.

    Google Scholar 

  26. A. Saxena, J.P. Tandon, Polyhedron 2 (1983) 443

    CAS  Google Scholar 

  27. D.L. Fox, J.T. Ruxer, R.M. Liver, K.L. Alford, R.N. Salvatore, Tetrahedron Lett. 45 (2004) 401.

    CAS  Google Scholar 

  28. For Reviews see: a) D. Chaturvedi, S. Ray, Curr. Org. Chem. 11 (2007) 987

    CAS  Google Scholar 

  29. D. Chaturvedi, N. Mishra, V. Mishra, Curr. Org. Synthesis 3 (2007) 308; For our research work see

    Google Scholar 

  30. D. Chaturvedi, A. Kumar, S. Ray, Synth. Commun. 32 (2002) 2651

    CAS  Google Scholar 

  31. D. Chaturvedi, A. Kumar, S. Ray, Tetrahedron Lett. 44 (2003) 7637

    CAS  Google Scholar 

  32. D. Chaturvedi, S. Ray, Tetrahedron Lett. 47 (2006) 1307

    CAS  Google Scholar 

  33. D. Chaturvedi, S. Ray, Tetrahedron Lett. 48 (2007) 149

    CAS  Google Scholar 

  34. D. Chaturvedi, N. Mishra, V. Mishra, Tetrahedron Lett. 48 (2007) 5043

    CAS  Google Scholar 

  35. D. Chaturvedi, N. Mishra, V. Mishra, Monatsh. Chem. 139 (2008) 267

    CAS  Google Scholar 

  36. D. Chaturvedi, N. Mishra, V. Mishra, Synthesis (2008) 355

    Google Scholar 

  37. D. Chaturvedi, S. Ray, Monatsh. Chem. 137 (2006) 201

    CAS  Google Scholar 

  38. D. Chaturvedi, S. Ray, Monatsh. Chem. 137 (2006) 311

    CAS  Google Scholar 

  39. D. Chaturvedi, S. Ray, Monatsh. Chem. 137 (2006) 459

    CAS  Google Scholar 

  40. D. Chaturvedi, S. Ray, Monatsh. Chem. 137 (2006) 465

    CAS  Google Scholar 

  41. D. Chaturvedi, S. Ray, Monatsh. Chem. 137 (2006) 1219.

    CAS  Google Scholar 

  42. D. Chaturvedi, S. Ray, Lett. Org. Chem. 2 (2005) 742

    CAS  Google Scholar 

  43. D. Chaturvedi, S. Ray, J. Sulfur Chem. 26 (2005) 365

    CAS  Google Scholar 

  44. D. Chaturvedi, S. Ray, J. Sulfur Chem. 27 (2006) 265

    Google Scholar 

  45. D. Chaturvedi, N. Mishra, V. Mishra, J. Sulfur Chem. 28 (2007) 39

    CAS  Google Scholar 

  46. D. Chaturvedi, N. Mishra, V. Mishra, Chinese Chem. Lett. 17 (2006) 1309

    CAS  Google Scholar 

  47. D. Chaturvedi, N. Mishra, V. Mishra, J. Sulfur Chem. 28 (2007) 607.

    Google Scholar 

  48. D. Chaturvedi, A. Kumar, S. Ray, Ind. J. Chem. Sec. B 42B (2004) 437.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. Chaturvedi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chaturvedi, D., Chaturvedi, A.K., Mishra, N. et al. Basic resin mediated efficient one-pot synthesis of carbazates from the corresponding alkyl halides. JICS 6, 510–513 (2009). https://doi.org/10.1007/BF03246528

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246528

Keywords

Navigation