Abstract
The alkylation of 5,5′-diaryl-2,2′-biimidazole-1,1′-diols with an equimolar amount of methyl iodide gave the corresponding N-methyl derivatives, and the reaction with 3 equiv of methyl iodide afforded alkylation products at the nitrogen atom and both hydroxy groups. 5,5′-Diaryl-1H,1′H-2,2′-biimidazoles were obtained by treatment of the title compounds with triphenylphosphine.
Similar content being viewed by others
REFERENCES
Nikitina, P.A. and Perevalov, V.P., Chem. Heterocycl.Compd., 2017, vol. 53, p. 123. https://doi.org/10.1007/s10593-017-2030-z
Tikhonov, A.Ya., Selivanov, B.A., and Gatilov, Yu.V., Tetrahedron Lett., 2015, vol. 56, p. 159. https://doi.org/10.1016/j.tetlet.2014.11.056
Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2020, vol. 56, p. 339. https://doi.org/10.1134/S107042802001027X
Shen, H.-Q., Wu, B., Xie, H.-P., and Zhou, Y.-G., Org. Lett., 2019, vol. 21, p. 2712. https://doi.org/10.1021/acs.orglett.9b00687
Matsumoto, S., Watanabe, M., and Akazome, M., Org. Lett., 2018, vol. 20, p. 3613. https://doi.org/10.1021/acs.orglett.8b01376
Structure Determination of Organic Compounds: Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed.
Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2017, vol. 53, p. 1239. https://doi.org/10.1134/S1070428017080139
Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2017, vol. 53, p. 236. https://doi.org/10.1134/S1070428017020166
Grigor’eva, L.N., Tikhonov, A.Ya., Amitina, S.A., Volodarskii, L.B., and Korobeinicheva, I.K., Chem. Heterocycl. Compd., 1986, vol. 22, p. 268. https://doi.org/10.1007/BF00514993
ACKNOWLEDGMENTS
The authors thank the Joint Chemical Service Center, Siberian Branch, Russian Academy of Sciences, for performing spectral and analytical measurements.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Osʼkina, I.A., Tikhonov, A.Y. 5,5′-Diaryl-2,2′-biimidazole-1,1′-diols: Reactions with Methyl Iodide and Triphenylphosphine. Russ J Org Chem 56, 1716–1719 (2020). https://doi.org/10.1134/S1070428020100073
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020100073