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Synthesis of 1,4- and 1,5-Diaryl-1H-Imidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

A simple method for the synthesis of 1,4- and 1,5-diarylimidazoles has been developed. The method is based on the condensation of appropriate α-diketone monooxime with aromatic amines and formaldehyde in the presence of boron trifluoride etherate leading to the formation of stable boron trifluoride complexes of imidazole N-oxides. Further reduction of these complexes led to the formation of corresponding imidazoles.

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References

  1. I. M. Pastor and M. Yus, Curr. Chem. Biol., 3, 65 (2009).

    Article  Google Scholar 

  2. T. Welton, Chem. Rev., 99, 2071 (1999).

    Article  CAS  Google Scholar 

  3. C. S. J. Cazin (editor), N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis, Springer, London (2011).

    Google Scholar 

  4. A. Kiyomori, J.-F. Marcoux, and S. L. Buchwald, Tetrahedron Lett., 40, 2657 (1999).

    Article  CAS  Google Scholar 

  5. H.-J. Cristau, P. P. Cellier, J.-F. Spindler, and M. Taillefer, Chem.-Eur. J., 10, 5607 (2004).

    Article  CAS  Google Scholar 

  6. L. Xu, D. Zhu, F. Wu, R. Wang, and B. Wan, Tetrahedron, 61, 6553 (2005).

    Article  CAS  Google Scholar 

  7. R. A. Altman and S. L. Buchwald, Org. Lett., 8, 2779 (2006).

    Article  CAS  Google Scholar 

  8. R. Altman, E. D. Koval, and S. L. Buchwald, J. Org. Chem., 72, 6190 (2007).

    Article  CAS  Google Scholar 

  9. J. P. Collman and M. Zhong, Org. Lett., 2, 1233 (2000).

    Article  CAS  Google Scholar 

  10. J. P. Collman, M. Zhong, C. Zhang, and S. J. Costanzo, J. Org. Chem., 66, 7892 (2001).

    Article  CAS  Google Scholar 

  11. J. P. Collman, M. Zhong, L. Zeng, and S. J. Costanzo, J. Org. Chem., 66, 1528 (2001).

    Article  CAS  Google Scholar 

  12. J.-B. Lan, L. Chen, X.-Q. Yu, J.-S. You, and R.-G. Xie, Chem. Commun., 188 (2004).

  13. S. Bojja, G. T. Venkanna, K. B. Shiva Kumar, and V. Balasubrahmanyam, Synthesis, 795 (2008).

  14. J. M. Khurana, G. C. Maikap, and S. Mehta, Synthesis, 731 (1990).

  15. K.-I. Nunami, M. Yamada, T. Fukui, and K. Matsumoto, J. Org. Chem., 59, 7635 (1994).

    Article  CAS  Google Scholar 

  16. A. R. Katritzky, D. Cheng, and R. P. Musgrave, Heterocycles, 44, 67 (1997).

    Article  CAS  Google Scholar 

  17. V. G. Pawar, W. M. De Borggraeve, K. Robeyns, L. Van Meervelt, F. Compernolle, and G. Hoornaert, Tetrahedron Lett., 47, 5451 (2006).

    Article  CAS  Google Scholar 

  18. G. V. Nikitina and M. S. Pevzner, Chem. Heterocycl. Compd., 29, 127 (1993). [Khim. Geterotsikl. Soedin., 147 (1993).]

  19. I. J. Ferguson and K. J. Schofield, Chem. Soc., Perkin Trans. 1, 275 (1975).

  20. R. Bartnic, W.E. Hahn, and G. Mloston, Rocz. Chem., 51, 49 (1977).

    Google Scholar 

  21. Н. Lettau, Z. Chem., 10, 462 (1970).

    Article  CAS  Google Scholar 

  22. M. Jasiński, G. Mlostoń, A. Linden, and H. Heimgartner, Helv. Chim. Acta, 91, 1916 (2008).

    Article  Google Scholar 

  23. G. Mlostoń, E. Obijalska, and H. Heimgartner, J. Fluorine Chem., 132, 951 (2011).

    Article  Google Scholar 

  24. G. Mlostoń, K. Urbaniak, A. Wojciechowska, A. Linden, and H. Heimgartner, Helv. Chim. Acta, 95, 577 (2012).

    Article  Google Scholar 

  25. R. Hossbach, H. Lettau, P. Nuhn, R. Schneider, P. Stanger, and B. Stiebitz, Pharmazie, 46, 412 (1991).

    CAS  Google Scholar 

  26. V. S. Mityanov, V. P. Perevalov, and I. I. Tkach, Chem. Heterocycl. Compd., 48, 1793 (2013). [Khim. Geterotsikl. Soedin., 1916 (2012).]

  27. V. S. Mityanov, L. G. Kuz'mina, V. P. Perevalov, and I. I. Tkach, Tetrahedron, 70, 3545 (2014).

    Article  CAS  Google Scholar 

  28. W. H. Hartung and J. C. Munch, J. Am. Chem. Soc., 51, 2262 (1929).

    Article  CAS  Google Scholar 

  29. H. Rheinboldt and O. Schmitz-Dumont, Justus Liebigs Ann. Chem., 444, 113 (1925).

    Article  CAS  Google Scholar 

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Correspondence to V. S. Mityanov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1669–1676, November, 2014.

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Mityanov, V.S., Perevalov, V.P. & Tkach, I.I. Synthesis of 1,4- and 1,5-Diaryl-1H-Imidazoles. Chem Heterocycl Comp 50, 1534–1540 (2015). https://doi.org/10.1007/s10593-014-1621-1

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  • DOI: https://doi.org/10.1007/s10593-014-1621-1

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