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Highly regioselective N-alkylation of benzotriazole under solvent-free conditions

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Abstract

An efficient, simple and solvent-free method for highly regioselective N-alkylation of benzotriazole in the presence of SiO2, K2CO3 and tetrabutylammonium bromide (TBAB) under thermal and microwave conditions has been described. In this method, 1-alkyl benzotriazoles were obtained regioselectively in moderate to high yields and short reaction times.

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References

  1. K. Tanaka, Solvent-free Organic Synthesis, Wiely-VCH, Weinheim, 2004

    Google Scholar 

  2. A. Loupy, Microwave in Organic Synthesis, Wiley-VCH, Weinheim, 2004.

  3. R.E. Deal, R.V. Kendall, Jpn. Kokai. (1978) 78121762, Chem. Abstr. 90 (1979) 98559

    Google Scholar 

  4. American Cyanamid Co. Belg. Patent (1977) 853179, Chem. Abstr. 88 (1978) 190843

    Google Scholar 

  5. J.L. Mokrosz, M.H. Paluchowska, E. Chojnacka-Wojcik, M. Filip, S. Charakchieva-Minol, A. Deren-Wesolek, M.J. Mokrosz, J. Med. Chem. 37 (1994) 2754

    CAS  Google Scholar 

  6. A.R. Katritzky, A.F. Pozharskii, Handbook of Heterocyclic Chemistry, 2th ed., Pergamon, New York, 2000

    Google Scholar 

  7. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles, Structures, Reactions, Synthesis and Applications, Wiley-VCH, GmbH and Co KGaA, Weinheim, 2003.

  8. A.R. Katritzky, B.V. Rogovoy, Chem.-Eur. J. 9 (2003) 4586

    CAS  Google Scholar 

  9. W. Peczynska-Czoch, F. Pognan, L. Kaczmarek, J. Boratynsky, J. Med. Chem. 37 (1994) 2503.

    Google Scholar 

  10. M.S. Gibson, J. Chem. Soc. (1956) 1076

  11. J. Bergman, P. Sand, Tetrahedron Lett. 25 (1984) 1957

    CAS  Google Scholar 

  12. L.J. Mathias, D. Burkett, Tetrahedron Lett. 20 (1979) 4709

    Google Scholar 

  13. H. Zhang, T. Hu, Y. Zhang, Q. Chen, Xiamen Daxue Xuebao, Ziran Kexuebano 38 (1999) 418 (Ch)

    CAS  Google Scholar 

  14. H. Zhang, Zhang, T. Hu, Q. Chen, Xiamen Daxue Xuebao, Ziran Kexuebano 38 (1999) 76 (Ch)

    CAS  Google Scholar 

  15. A.R.Katritzky, J. Wu, Synthesis (1994) 597

  16. A.R. Katritzky, D.C. Oniciu, I. Ghiriviga, Synth. Commun. 27 (1997) 1613

    CAS  Google Scholar 

  17. N. Arnau, Y. Arredona, M. Moreno-Mañas, R. Pleixats, M. Villarroya, J. Heterocyc. Chem. 32 (1995) 1325

    CAS  Google Scholar 

  18. I.P. Beletskaya, D.V. Davydov, M. Moreno-Mañas, Tetrahedron Lett. 39 (1998) 5621

    CAS  Google Scholar 

  19. I.P. Beletskaya, D.V. Davydov, M. Moreno-Mañas, Tetrahedron Lett. 39 (1998) 5617

    CAS  Google Scholar 

  20. P. López-Alvarado, C. Avendaño, J.C. Menéndez, J. Org. Chem. 60 (1995) 5678

    Google Scholar 

  21. Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, J. Chem. Res. (2004) 344.

  22. N. L. Miller, E.C. Wagner, J. Am. Chem. Soc. 76 (1954) 1847

    CAS  Google Scholar 

  23. K. Sukata, Bull. Chem. Soc. Jpn. 56(1983) 280

    CAS  Google Scholar 

  24. M. Märky, H. Schmid, H.-J. Hansen, Helv. Chim. Acta 62 (1979) 2129.

    Google Scholar 

  25. A. Khalafi-Nezhad, A. Parhami, M.N. Soltani Rad, A. Zare, Tetrahedron Lett. 46 (2005) 6879

    CAS  Google Scholar 

  26. A.Khalafi-Nezhad, A. Zare, M.N. Soltani Rad, B. Mokhtari, A. Parhami, Synthesis (2005) 419

  27. A. Khalafi-Nezhad, B. Mokhtari, Tetrahedron Lett. 45 (2004) 6737

    CAS  Google Scholar 

  28. A. Khalafi-Nezhad, M.N. Soltani Rad, A. Khoshnood, Synthesis (2004) 583

  29. A. Khalafi-Nezhad, M.N. Soltani Rad, G.H. Hakimelahi, Helv. Chim. Acta 86 (2003) 2396

    CAS  Google Scholar 

  30. A. Khalafi-Nezhad, B. Mokhtari, M.N. Soltani Rad, Tetrahedron Lett. 44 (2003) 7325

    CAS  Google Scholar 

  31. A. Khalafi-Nezhad, F. Alamdari, N. Zekri, Tetrahedron 56 (2000) 7503

    CAS  Google Scholar 

  32. A. Khalafi-Nezhad, A. Hashemi, J. Chem. Res., Synop (1999) 720.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    A. Khalafi-Nezhad, A. Parhami & G. R. Nejabat

  2. Department of Chemistry, Payame Nour University of Bushehr, Bushehr, 1698, Iran

    A. Zare

  3. Department of Chemistry, College of Basic Sciences, Shiraz University of Technology, Shiraz, 71555-313, Iran

    M. N. Soltani Rad

Authors
  1. A. Khalafi-Nezhad
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  2. A. Zare
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  3. A. Parhami
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  4. M. N. Soltani Rad
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  5. G. R. Nejabat
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Correspondence to A. Khalafi-Nezhad or A. Zare.

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Khalafi-Nezhad, A., Zare, A., Parhami, A. et al. Highly regioselective N-alkylation of benzotriazole under solvent-free conditions. JICS 4, 271–278 (2007). https://doi.org/10.1007/BF03245976

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  • DOI: https://doi.org/10.1007/BF03245976

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