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Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2

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Abstract

A combination of trichloromelamine and sodium nitrite in the presence of wet silica gel was used as an effective nitrosating agent for the transformation of secondary amines into the corresponding N-nitroso derivatives under mild and heterogeneous conditions in good to excellent yields.

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References

  1. Williams, D.L.H., Nitrosation, Cambridge: Cambridge Univ., 1988, p. 77.

    Google Scholar 

  2. Williams, D.L.H., The Chemistry of Amino, Nitroso, Nitro, and Related Groups, Patai, S., Ed., Chichester: Wiley, 1996, p. 665.

    Chapter  Google Scholar 

  3. Keefer, L.K. and Williams, D.L.H., Methods in Nitric Oxide Research, Feelisch, M. and Stamler, J.S., Eds., Chichester: Wiley, 1996, p. 509.

    Google Scholar 

  4. Garcia-Rio, L., Leis, J.R., Moreira, J.A., and Norberto, F., J. Org. Chem., 2001, vol. 66, p. 381.

    Article  CAS  Google Scholar 

  5. Garcia-Rio, L., Leis, J.R., and Iglesias, E., J. Org. Chem., 1997, vol. 62, p. 4712.

    Article  CAS  Google Scholar 

  6. Nudelman, N.S. and Bonatti, A.E., Synlett, 2000, p. 1825.

  7. Olszewska, T., Milewska, M.J., Gdaniec, M., Matuszynska, H., and Potonski, T., J. Org. Chem., 2001, vol. 66, p. 501.

    Article  CAS  Google Scholar 

  8. Zolfigol, M.A., Shirini, F., Ghorbani Choghamarani, A., Taqian-nasab, A., Keypour, H., and Salehzadeh, S., J. Chem. Res., Synop., 2000, p. 420.

  9. Rivera, A., Gallo, G.I., and Joseph-Nathan, P., Synth. Commun., 1997, vol. 27, p. 163.

    Article  CAS  Google Scholar 

  10. Furniss, B.S., Hannaford, A.J., Smith, P.W.G., and Tatchell, A.R., Vogel’s Textbook of Practical Organic Chemistry, Including Qualitative Organic Analysis, London: Longman Scientific & Technical, 1989, 5th ed.

    Google Scholar 

  11. Shriner, R.L., Reynold, T.L., Fuson, C., Curtin, D.Y., and Morrill, T.C., The Systematic Identification of Organic Compounds: A Laboratory Manual, New York: Wiley, 1980, 6th ed., p. 220.

    Google Scholar 

  12. Castedo, L., Riguera, R., and Vezquez, M.P., J. Chem. Soc., Chem. Commun., 1983, p. 301.

  13. Fanning, J.C., Keefer, L.K., and Larry, K., J. Chem. Soc., Chem. Commun., 1987, p. 955.

  14. Nakajima, M., Warner, J.C., and Anselme, J.P., Tetrahedron Lett., 1984, vol. 25, p. 2619.

    Article  CAS  Google Scholar 

  15. Chang, S.K., Harrington, G.W., Rothstein, M., Shergalis, W.A., Swern, D., and Vohra, S.K., Cancer Res., 1979, vol. 39, p. 3871.

    CAS  Google Scholar 

  16. Makhova, N.N., Karpov, G.A., Mikhailyuk, A.N., Bova, A.E., Khmel’nitskii, L.I., and Novikov, S.S., Izv. Akad. Nauk SSSR, Ser. Khim., 1978, no. 1, p. 226.

  17. Zolfigol, M.A., Zebarjadian, M.H., Chehardoli, G.A., Keypour, H., Salehzadeh, S., and Shamsipur, M., J. Org. Chem., 2001, vol. 66, p. 3619.

    Article  CAS  Google Scholar 

  18. Zolfigol, M.A., Synth. Commun., 1999, vol. 29, p. 905.

    Article  CAS  Google Scholar 

  19. Zolfigol, M.A., Ghorbani-Choghamarani, A., and Hazarkhani, H., Synlett, 2002, p. 1002.

  20. Zolfigol, M.A. and Bamoniri, A., Synlett, 2002, p. 1621.

  21. Zolfigol, M.A., Habibi, D., Mirjalili, B.F., and Bamoniri, A., Tetrahedron Lett., 2003, vol. 44, p. 3345.

    Article  CAS  Google Scholar 

  22. Hou, J.Y., Wang, Y.L., and Wang, J.Y., J. Chem. Res., Synop., 2003, p. 626.

  23. Iranpoor, N., Firouzabadi, H., and Pourali, A.R., Synthesis, 2003, p. 1591.

  24. Jin, D. and Mendehall, D., Tetrahedron Lett., 1996, vol. 37, p. 4881.

    Article  CAS  Google Scholar 

  25. Singer, S.S., Lijinsky, W., and Singer, G.M., Tetrahedron Lett., 1977, vol. 18, p. 1613.

    Article  Google Scholar 

  26. Singer, S.S., J. Org. Chem., 1978, vol. 43, p. 4612.

    Article  CAS  Google Scholar 

  27. Turnbull, K., J. Heterocycl. Chem., 1985, vol. 22, p. 965.

    Article  CAS  Google Scholar 

  28. Richter-Addo, G.B., Acc. Chem. Res., 1999, vol. 32, p. 529.

    Article  CAS  Google Scholar 

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Correspondence to A. Bamoniri.

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Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 9, pp. 1397–1400.

The text was submitted by the authors in English.

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Bamoniri, A., Zolfigol, M.A., Mirjalili, B.F. et al. Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2 . Russ J Org Chem 43, 1393–1396 (2007). https://doi.org/10.1134/S1070428007090229

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  • DOI: https://doi.org/10.1134/S1070428007090229

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