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Specific Features of the Reduction of 7-Nitro-9-R-2,3-dihydroimidazo[1,2-a]benzimidazoles with SnCl2 in Hydrochloric Acid

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Abstract

The reduction of 7-nitro-N(9)-substituted 2,3-dihydroimidazo[1,2-a]benzimidazoles with SnCl2 in conc. HCl forms a mixture of the previously unknown 7-amino and 7-amino-6-chloro derivatives in a ratio depending on the nature of the substituent at position 9. This result gave grounds to assume that not the final heteroarylamine, but the intermediate heteroarylhydroxylamine formed by a mechanism similar to the acid-induced Bamberger rearrangement of arylhydroxylamines, is subjected to chlorination.

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Notes

  1. Primed numbers denote carbon atoms of the exocyclic ethylene group of the side chain.

REFERENCES

  1. Spasov, A.A., Anisimova, V.A., Petrov, V.I., Kucheryavenko, A.F., Tolpygin, I.E., and Minkin, V.I., RF Patent no. 2453312, 2010; Byull. Izobret., 2012, no. 17.

  2. Anisimova, V.A., Balabolkin, M.I., Vdovina, G.P., Dedov, I.I., Minkin, V.I., Petrov, V.I., and Spasov, A.A., RF Patent no. 2386634, 2007; Byull. Izobret., 2010, no. 11.

  3. Anisimova, V.A., Tolpygin, I.E., Spasov, A.A., Kosolapov, V.A., Stepanov, A.V., and Kucheryavenko, A.F., Pharm. Chem. J., 2006, vol. 40, p. 261. https://doi.org/10.1007/s11094-006-0105-8

    Article  CAS  Google Scholar 

  4. Oh, S., Kim, S., Kong, S., Yang, G., Lee, N., Han, D., Goo, J., Siqueira-Neto, J.L., Freitas-Junior, L.H., and Song, R., Eur. J. Med. Chem., 2014, vol. 84, p. 395. https://doi.org/10.1016/j.ejmech.2014.07.038

    Article  CAS  PubMed  Google Scholar 

  5. Khan, K.M., Shah, Z., Ahmad, V.U., Ambreen, N., Khan, M., Taha, M., Rahim, F., Noreen, S., Perveen, S., Choudhary, M.I., and Voelter, W., Bioorg. Med. Chem., 2012, vol. 20, p. 1521. https://doi.org/10.1016/j.bmc.2011.12.041

    Article  CAS  PubMed  Google Scholar 

  6. North, R.J. and Day, A.R., J. Heterocycl. Chem., 1969, vol. 6, p. 655. https://doi.org/10.1002/jhet.5570060511

    Article  CAS  Google Scholar 

  7. Dubois, L., Evanno, Y., Even, L., Gille, C., Malanda, A., Machnik, D., and Rakotoarisoa, N., WO Patent Appl. no. WO 2007088277, 2007.

  8. Sochnev, V.S., Kuz’menko, T.A. Morkovnik, A.S., Divaeva, L.N., Podobina, A.S., Zubenko, A.A., Chepurnoy, P.B., Borodkin, G.S., and Klimenko, A.I., Mendeleev Commun., 2021, vol. 31, p. 555. https://doi.org/10.1016/j.mencom.2021.07.040

    Article  CAS  Google Scholar 

  9. Simonov, A.M., Koshchienko, Yu.V., Poludnenko, V.G., Khorunzhev, V.E., Chem. Heterocycl. Compd., 1970, vol. 6, p. 1313. https://doi.org/10.1007/BF00755086

    Article  Google Scholar 

  10. Wishart, D.S., Knox, C., Guo, A.C., Shrivastava, S., Hassanali, M., Stothard, P., Chang, Z., and Woolsey, J., Nucleic Acids Res., 2006, vol. 34, p. 668. https://doi.org/10.1093/nar/gkj067

    Article  CAS  Google Scholar 

  11. De Kiewiet, T.E. and Stephen, H., J. Chem. Soc., 1931, p. 82. https://doi.org/10.1039/JR9310000082

  12. Hussni, A.M., Tetrahedron, 1996, vol. 52, p. 8863. https://doi.org/10.1016/0040-4020(96)00433-4

    Article  Google Scholar 

  13. Bamberger, E., Chem. Ber., 1894, vol. 27, p. 1548. https://doi.org/10.1002/cber.18940270276

    Article  CAS  Google Scholar 

  14. Yamabe, Sh. and Yamazaki, Sh., J. Phys. Org. Chem., 2016, vol. 29, p. 361. https://doi.org/10.1002/poc.3543

    Article  CAS  Google Scholar 

  15. Yamabe, Sh., Zeng, G., Guan, W., and Sakaki, Sh., Beilstein J. Org. Chem., 2013, vol. 9, p. 1073. https://doi.org/10.3762/bjoc.9.119

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Gel’man, N.E., Terent’eva, E.A., Shanina, T.M., and Kiparenko, L.M., Metody kolichestvennogo organicheskogo elementnogo analiza (Methods for Quantitative Organic Elemental Analysis), Moscow: Khimiya, 1987.

  17. Granovsky, A.A., Firefly version 8. http://classic.chem.msu.su/gran/gamess/index.html

  18. Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347.

    Article  CAS  Google Scholar 

  19. Di Braccio, M., Grossi, G., Signorello, M.G., Leoncini, G., Cichero, E., Fossa, P., Alfei, S., and Damonte, G., Eur. J. Med. Chem., 2013, vol. 62, p. 564. https://doi.org/10.1016/j.ejmech.2013.01.026

    Article  CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The spectra were measured using the equipment of the “Molecular Spectroscopy” Center for Collective Use, Southern Federal University.

Funding

The work was financially supported by the Ministry of Science and Higher Education of the Russian Federation in through the state assignment for the Southern Federal University no. FENW-2020-0031 (0852-2020-0031).

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 344090, Rostov-on-Don, Russia

    V. S. Sochnev, T. A. Kuz’menko, A. S. Morkovnik & Yu. V. Koshchienko

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  1. V. S. Sochnev
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  2. T. A. Kuz’menko
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  3. A. S. Morkovnik
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  4. Yu. V. Koshchienko
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Correspondence to V. S. Sochnev.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 5, pp. 495–501 https://doi.org/10.31857/S0514749222050068.

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Sochnev, V.S., Kuz’menko, T.A., Morkovnik, A.S. et al. Specific Features of the Reduction of 7-Nitro-9-R-2,3-dihydroimidazo[1,2-a]benzimidazoles with SnCl2 in Hydrochloric Acid. Russ J Org Chem 58, 679–684 (2022). https://doi.org/10.1134/S1070428022050062

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