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.
Similar content being viewed by others
References
I. M. Pastor and M. Yus, Curr. Chem. Biol., 1, 65 (2009).
M. Yamada, T. Yura, M. Morimoto, T. Harada, K. Yamada, Y. Honma, M. Kinoshita, and M. Sugiura, J. Med. Chem., 39, 596 (1996).
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).
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).
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).
A. Kiyomori, J.-F. Marcoux, and S. I. Buchwald, Tetrahedron Lett., 40, 2657 (1999).
J. P. Collman, M. Zhong, I. Zeng, and S. Costanzo, J. Org. Chem., 66, 1528 (2001).
J. M. Khurana, G. C. Maikap, and S. Mehta, Synthesis, 731 (1990).
K.-I. Nunami, M. Yamada, T. Fukui, and K. Matsumoto, J. Org. Chem., 59, 7635 (1994).
A. R. Katritzky, D. Cheng, and R. P. Musgrave, Heterocycles, 44, 67 (1997).
V. G. Pawar, W. M. De Borggraeve, K. Robeyns, L. Van Meervelt, F. Compernolle, and G. Hoornaert, Tetrahedron Lett., 47, 5451 (2006).
I. J. Ferguson and K. Schofield, J. Chem. Soc., Perkin Trans. 1, 275 (1975).
R. Bartnic, W. E. Hahn, and G. Mloston, Rocz. Chem., 51, 49 (1977).
H. Lettau, Z. Chem., 10, 462 (1970).
H. Cerecetto, A. Gerpe, and M. González, Synthesis, 2678 (2004).
J. Alcázar, M. Begtrup, and A. de la Hoz, J. Chem. Soc., Perkin Trans. 1, 2467 (1995).
M. A. Sprung, Chem. Rev., 26, 297 (1940).
G. V. Nikitina and M. S. Pevzner, Khim. Geterotsikl. Soedin., 147 (1993). [Chem. Heterocycl. Compd., 29, 127 (1993)].
Y. Fukui, Y. Kuwahara, K. Saheki, and M. Mori, Yakugaku Zasshi, 80, 1472 (1960).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1916-1923, December, 2012.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1210-8