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Synthesis of 2-unsubstituted 1-arylimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

A method has been developed for the synthesis of 1-arylimidazoles lacking a substituent at position 2, featuring the preparation of 1-arylimidazole N-oxides stabilized as boron trifluoride derivatives, with subsequent reduction to the desired imidazoles. This method permits broad variation of the substituents in the aryl part of these molecules.

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References

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

    Article  Google Scholar 

  2. M. Yamada, T. Yura, M. Morimoto, T. Harada, K. Yamada, Y. Honma, M. Kinoshita, and M. Sugiura, J. Med. Chem., 39, 596 (1996).

    Article  CAS  Google Scholar 

  3. L. Wang, K. W. Woods, Q. Li, K. J. Barr, R. W. McCroskey, S. M. Hannick, L. Gherke, R. B. Credo, Y.-H. Hui, K. Marsh, R. Warner, J. Y. Lee, N. Zielinski-Mozng, D. Frost, S. H. Rosenberg, and H. L. Sham, J. Med. Chem., 45, 1697 (2002).

    Article  CAS  Google Scholar 

  4. J. L. Romine, S. W. Martin, V. K. Gribkoff, C.G. Boissard, S. I. Dworetzky, J. Natale, Y. Li, Q. Gao, N. A. Meanwell, and J. E. Starrett, J. Med. Chem., 45, 2942 (2002).

    Article  CAS  Google Scholar 

  5. C. Almansa, J. Alfón, A. F. De Arriba, F. L. Cavalcanti, I. Escamilla, L. A. Gómez, A. Miralles, R. Soliva, J. Bartoli, E. Carceller, M. Merlos, and J. Garcia-Rafanell, J. Med. Chem., 46, 3463 (2003).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. 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 

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

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

    Google Scholar 

  14. H. Lettau, Z. Chem., 10, 462 (1970).

    Article  CAS  Google Scholar 

  15. H. Cerecetto, A. Gerpe, and M. González, Synthesis, 2678 (2004).

  16. J. Alcázar, M. Begtrup, and A. de la Hoz, J. Chem. Soc., Perkin Trans. 1, 2467 (1995).

  17. M. A. Sprung, Chem. Rev., 26, 297 (1940).

    Article  CAS  Google Scholar 

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

    Google Scholar 

  19. Y. Fukui, Y. Kuwahara, K. Saheki, and M. Mori, Yakugaku Zasshi, 80, 1472 (1960).

    CAS  Google Scholar 

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Correspondence to V. S. Mityanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1916-1923, December, 2012.

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Mityanov, V.S., Perevalov, V.P. & Tkach, I.I. Synthesis of 2-unsubstituted 1-arylimidazoles. Chem Heterocycl Comp 48, 1793–1800 (2013). https://doi.org/10.1007/s10593-013-1210-8

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  • DOI: https://doi.org/10.1007/s10593-013-1210-8

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