Skip to main content

Advertisement

SpringerLink
Log in

A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate

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

Abstract

A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7

Similar content being viewed by others

References

  1. A. Albini, S. Pietra, Heterocyclic N-oxides (CRC Press, Boca Raton, 1991)

    Google Scholar 

  2. A. Albini, Synthesis 3, 263–277 (1993)

    Article  Google Scholar 

  3. J.H. Boyer, Chem. Rev. 80, 495–561 (1980)

    Article  CAS  Google Scholar 

  4. M. Schroder, Chem. Rev. 80, 187–213 (1980)

    Article  Google Scholar 

  5. B. Sain, S.L. Jain, Angew. Chem. 42, 1265–1267 (2003)

    Article  Google Scholar 

  6. S.L. Jain, B. Sain, Chem. Commun. (2002). https://doi.org/10.1039/B202744P

    Article  Google Scholar 

  7. K. Bergstad, J.E. Backvall, J. Org. Chem. 63, 6650–6655 (1998)

    Article  CAS  Google Scholar 

  8. S.-I. Murahashi, Pure Appl. Chem. 64, 403–577 (1992)

    Article  CAS  Google Scholar 

  9. C. Coperet, H. Adolfsson, T.-A. V. Khuong, A. K. Yudin, K. B. Sharpless, J. Org. Chem. 63, 1740–1741 (1998)

    Article  CAS  Google Scholar 

  10. Y. Jiao, Y. Hongtao, Synlett 1, 73–74 (2001)

    Article  Google Scholar 

  11. J. Rudolph, K.L. Reddy, J.P. Chiang, K.B. Sharpless, J. Am. Chem. Soc. 119, 6185–6188 (1997)

    Article  Google Scholar 

  12. D.J. Robinson, P. McMom, D. Bethell, P.C. Bulmanpage, C. Sly, F. King, F.E. Hangcock, G.J. Hutching, Catal. Lett. 72, 233–234 (2001)

    Article  CAS  Google Scholar 

  13. B.M. Choudary, B. Bharathi, Ch.V. Reddy, M.L. Kantam, K.V. Raghavan, Chem. Commun. (2001). https://doi.org/10.1039/B104754J

    Article  Google Scholar 

  14. H. Masashi, H. Hirotoshi, Sumitiomo Chemical Co., Ltd, Japanese Patent JP 2004307473 (2004)

  15. A. Thellend, P. Battioni, W. Sanderson, D. Mansuy, Synthesis 12, 1387–1388 (1997)

    Article  Google Scholar 

  16. A.J. Bailey, W.P. Griffith, B.C. Parkin, J. Chem. Soc. Dalton Trans. (1995) https://doi.org/10.1039/DT9950001833

    Article  Google Scholar 

  17. L. Franz, L. Andre, D. Paul, European Patent EP 224662 (1986)

  18. N. Hirofumi, Japanese Patent JP 09087251 (1995)

  19. L. Rout, T. Punniyamurthy, Adv. Synth. Catal. 347, 1958–1960 (2005)

    Article  CAS  Google Scholar 

  20. G.B. Payne, P.H. Deming, P.H. Williams, J. Org. Chem. 26, 659–663 (1961)

    Article  CAS  Google Scholar 

  21. A.R. Gallopo, J.O. Edwards, Kinetics and mechanism of the oxidation of pyridine by Caro’s acid catalyzed by ketones. J. Org. Chem. 46, 1684–1688 (1981)

    Article  CAS  Google Scholar 

  22. S. Youssif, Recent trends in the chemistry of pyridine N-oxides. ARKIVOC 242–268 (2001)

  23. M. Ferrer, F. Sanchez-Baeza, A. Messgure, Tetrahedron 53, 15877–15888 (1997)

    Article  CAS  Google Scholar 

  24. Z. Zhu, J.H. Espenson, J. Org. Chem. 60, 7728–7732 (1995)

    Article  CAS  Google Scholar 

  25. R.W. Murray, K. Iyanar, J. Chen, J.T. Wearing, Tetrahedron Lett. 37, 805–808 (1996)

    Article  CAS  Google Scholar 

  26. A.L. Baumstark, M. Dotrong, P.C. Vasquez, Tetrahedron Lett. 28, 1963–1966 (1987)

    Article  CAS  Google Scholar 

  27. H.S. Mosher, L. Turner, A. Carlsmith, Org. Synth. Coll. 4, 828–830 (1963)

    Google Scholar 

  28. R. Bernardi, B. Novo, G. Resnati, J. Chem. Soc. Perkin Trans. 1 (1996). https://doi.org/10.1039/P19960002517

  29. P. Brougham, M.S. Cooper, D.A. Cummerson, H. Heaney, N. Thomson, Synthesis 11, 1015–1017 (1987)

    Article  Google Scholar 

  30. M.M. Khodaei, K. Bahrami, A. Karimi, Synthesis 11, 1682–1684 (2008)

    Article  CAS  Google Scholar 

  31. S. Oae, Lect. Heterocycl. Chem. 4, 69–73 (1978)

    CAS  Google Scholar 

  32. P. Kulanthaivel, R.J. Barbuch, R.S. Davidson, P.Y. Gregory, A. Rener, E.L. Mattiuz, C.E. Hadden, L.A. Goodwin, W.J. Ehlhardt, Drug. Metab. Dispos. 32, 966–972 (2004)

    CAS  PubMed  Google Scholar 

  33. S. Donck, E. Gravel, N. Shah, D.V. Jawale, E. Doris, I.N.N. Namboothiri, RSC Adv. 5, 50865–50868 (2015)

    Article  CAS  Google Scholar 

  34. P.M. Reis, B. Roya, Tetrahedron Lett. 50, 949–952 (2009)

    Article  CAS  Google Scholar 

  35. B.W. Yoo, J.W. Choi, D.Y. Kim, S.K. Hwang, K.I. Choi, J.H. Kim, Bull. Korean Chem. Soc. 23, 797–798 (2002)

    Article  CAS  Google Scholar 

  36. J.S. Yadav, B.V. Subba Reddy, M. Muralidhar Reddy, Tetrahedron Lett. 41, 2663–2665 (2000)

    Article  CAS  Google Scholar 

  37. B. Jousseaume, E. Chanson, Synthesis 1, 55–56 (1987)

    Article  Google Scholar 

  38. R. Baliki, Synthesis 8, 645–646 (1989)

    Article  Google Scholar 

  39. P. Ilankumaran, S. Chandrasekara, Tetrahedron Lett. 36, 4881–4882 (1995)

    Article  CAS  Google Scholar 

  40. Y. Handa, W. Tanaka, A. Ohta, J. Chem. Soc. Chem. Commun. 59, 1225–1226 (1994)

    Google Scholar 

  41. J.B. Hendrickson, S.M. Schwartzman, Tetrahedron Lett. 16, 277–280 (1975)

    Article  Google Scholar 

  42. D. Crich, H. Dyker, Tetrahedron Lett. 30, 475–476 (1989)

    Article  CAS  Google Scholar 

  43. A. Aaberg, T. Gramstad, S. Husebye, Tetrahedron Lett. 20, 2263–2264 (1979)

    Article  Google Scholar 

  44. J.B. Hendrickson, M.S. Hussoin, J. Org. Chem. 54, 1144–1149 (1989)

    Article  CAS  Google Scholar 

  45. S. Caddick, J.D. Wilden, D.B. Judd, J. Am. Chem. Soc. 126, 1024–1025 (2004)

    Article  CAS  PubMed  Google Scholar 

  46. S.-L. You, J.W. Kelly, Tetrahedron 61, 241–249 (2005)

    Article  CAS  Google Scholar 

  47. Y. Liang, X. Jiang, Z.-X. Yu, Org. Lett. 11, 5302–5305 (2009)

    Article  CAS  PubMed  Google Scholar 

  48. J. Xi, Q.-L. Dong, J. Liu, G.-S. Liu, L. Chen, Z.-J. Yao, Synlett 11, 1674–1678 (2010)

    Google Scholar 

  49. P. Xu, G-S. Liu, J. Xi, S. Wang, Z.-J. Yao, Tetrahedron 67, 5455–5460 (2011)

    Article  CAS  Google Scholar 

  50. Z. Moussa, ARKIVOC 2012, 432–490 (2012)

  51. J.I. McCauley, Synlett 2999–3000 (2012)

  52. M.M. Khodaei, E. Nazari, Synthesis of diarylmethanes via a Friedel-Crafts benzylation using arenes and benzyl alcohols in the presence of triphenylphosphine ditriflate. Tetrahedron Lett. 53, 5131–5135 (2012)

    Article  CAS  Google Scholar 

  53. S. You, H. Razavi, Y.J.W. Kell, Angew. Chem. Int. Ed. 42, 83–85 (2003)

    Article  CAS  Google Scholar 

  54. F. Yang, X. Zhang, F. Li, Z. Wang, L. Wang, Green Chem. 18, 3518–3521 (2016)

    Article  CAS  Google Scholar 

  55. D. Azarifar, B. Mahmoudi, J. Iran. Chem. Soc. 13, 645–651 (2016)

    Article  CAS  Google Scholar 

  56. Q.F. Li, W. Luo, W. Lu, Z. Wang, React. Kinet. Mech. Catal. 119, 235–243 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research was supported by the Research Council of the Razi University in Iran.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Razi University, Kermanshah, 67149-67346, Iran

    Mohammad Mehdi Khodaei, Abdolhamid Alizadeh & Hadis Afshar Hezarkhani

Authors
  1. Mohammad Mehdi Khodaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Abdolhamid Alizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hadis Afshar Hezarkhani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Mehdi Khodaei.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 958 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khodaei, M.M., Alizadeh, A. & Hezarkhani, H.A. A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate. J IRAN CHEM SOC 15, 1843–1849 (2018). https://doi.org/10.1007/s13738-018-1381-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-018-1381-4

Keywords

Search

Navigation