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Reaction of 5,5′-Diaryl-1,1′-dihydroxy-2,2′-biimidazoles with Trimethyl Phosphite

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Abstract

The reaction of 5,5′-diaryl-1H,1H-[2,2′-biimidazole]-1,1′-diols with trimethyl phosphite gave the cor­responding 4′,5-diaryl-1′,4,5′-trimethyl-1H,1′H-[2,2′-biimidazol]-1-ols and 4,5′-diaryl-1,4′,5-trimethyl-1H,1′H-2,2′-biimidazoles. The structure of the synthesized compounds was determined using various NMR correlation techniques (1H–1H COSY, 1H–13C HSQC, 1H–13C HMBC, 1H–1H NOESY).

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REFERENCES

  1. Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2020, vol. 56, p. 1716. https://doi.org/10.1134/S1070428020100073

    Article  Google Scholar 

  2. Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2020, vol. 56, p. 339. https://doi.org/10.1134/S107042802001027X

    Article  Google Scholar 

  3. 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

    Article  CAS  PubMed  Google Scholar 

  4. Matsumoto, S., Watanabe, M., and Akazome, M., Org. Lett., 2018, vol. 20, p. 3613. https://doi.org/10.1021/acs.orglett.8b01376

    Article  CAS  PubMed  Google Scholar 

  5. Xiao, J.-C. and Shreeve, J.M., J. Org. Chem., 2005, vol. 70, p. 3072. https://doi.org/10.1021/jo0501083

    Article  CAS  PubMed  Google Scholar 

  6. Casas, J.S., Castineiras, A., Parajo, Y., Sanchez, A., Sanchez-Gonzalez, A., and Sordo, J., Polyhedron, 2005, vol. 24, p. 1196. https://doi.org/10.1016/j.poly.2005.04.008

    Article  CAS  Google Scholar 

  7. Murata, T., Nakasuji, K., and Morita, Y., Eur. J. Org. Chem., 2012, vol. 2012, p. 4123. https://doi.org/10.1002/ejoc.201200426

    Article  CAS  Google Scholar 

  8. Van Hirschheydt, T. and Voss, E., US Patent Appl. Pub. no. 20050085473, 2005; Chem. Abstr., 2005, vol. 142, no. 411373.

  9. Semones, M., Feng, Y., Johnson, N., Adams, J.L., Winkler, J., and Hansbury, M., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4756. https://doi.org/10.1016/j.bmcl.2007.06.068

    Article  CAS  PubMed  Google Scholar 

  10. Kim, D.-K., Lee, Y.-I., Lee, Y.W., Dewang, P.M., Sheen, Y.Y., Kim, Y.W., Park, H.-J., Yoo, J., Lee, H.S., and Kim, Y.-K., Bioorg. Med. Chem., 2010, vol. 18, p. 4459. https://doi.org/10.1016/j.bmc.2010.04.071

    Article  CAS  PubMed  Google Scholar 

  11. Nikitina, P.A., Kuz’mina, L.G., Perevalov, V.P., and Tkach, I.I., Tetrahedron, 2013, vol. 69, p. 3249. https://doi.org/10.1016/j.tet.2013.02.039

    Article  CAS  Google Scholar 

  12. Arvanitis, A.G., Rodgers, J.D., Combs, A.P., Sparks, R.B., Robinson, D.J., Fridman, J.S., and Vaddi, K., Int. Patent Appl. Pub. no. WO2007038215, 2007; Chem. Abstr., 2007, vol. 146, no. 401967.

  13. Liverton, N.J., Butcher, J.W., Claiborne, C.F., Claremon, D.A., Libby, B.E., Nguyen, K.T., Pitzen­berger, S.M., Selnick, H.G., Smith, G.R., Tebben, A., Vacca, J.P., Varga, S.L., Agarwal, L., Dancheck, K., Forsyth, A.J., Fletcher, D.S., Frantz, B., Hanlon, W.A., Harper, C.F., Hofsess, S.J., Kostura, M., Lin, J., Luell, S., O’Neill, E.A., Orevillo, C.J., Pang, M., Parsons, J., Rolando, A., Sahly, Y., Visco, D.M., and O’Keefe, S.J., J. Med. Chem., 1999, vol. 42, p. 2180. https://doi.org/10.1021/jm9805236

    Article  CAS  PubMed  Google Scholar 

  14. Gornostaev, L.M., Vigant, M.V., Kargina, O.I., Kuznetsova, A.S., Khalyavina, Yu.G., and Lavriko­va, T.I., Russ. J. Org. Chem., 2013, vol. 49, p. 1369. https://doi.org/10.1134/S1070428013090194

    Article  CAS  Google Scholar 

  15. Nikolaenkova, E.B., Os’kina, I.A., and Tikhonov, A.Y., Russ. J. Org. Chem., 2017, vol. 53, p. 1887. https://doi.org/10.1134/S1070428017120193

    Article  CAS  Google Scholar 

  16. Kuz’menko, I.I., Bobkov, V.N., and Zvolinskaya, T.V., Russ. J. Gen. Chem., 1989, vol. 59, p. 1557.

    Google Scholar 

  17. Fulmer, G.R., Miller, A.J.M., Sherden, N.H., Gottlieb, H.E., Nudelman, A., Stoltz, B.M., Bercaw, J.E., and Goldberg, K.I., Organometallics, 2010, vol. 29, p. 2176. https://doi.org/10.1021/om100106e

    Article  CAS  Google Scholar 

  18. Nikolaenkova, E.B., Tikhonov, A.Ya., and Grishchen­ko, S.Yu., Chem. Heterocycl. Compd., 2019, vol. 55, p. 142. https://doi.org/10.1007/s10593-019-02430-8

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank the joint chemical service center, Siberian Branch, Russian Academy of Sciences, for performing spectral and analytical studies.

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Correspondence to I. A. Os’kina.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 89–95 https://doi.org/10.31857/S0514749222010098.

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Krasnov, V.I., Os’kina, I.A. & Tikhonov, A.Y. Reaction of 5,5′-Diaryl-1,1′-dihydroxy-2,2′-biimidazoles with Trimethyl Phosphite. Russ J Org Chem 58, 70–75 (2022). https://doi.org/10.1134/S1070428022010092

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