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Vicarious nucleophilic amination of five-membered 4,6-dinitrobenzoheterocycles

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abstract

Reactions of isomeric 4,6-dinitro-1- and 4,6-dinitro-2-phenylindazoles, as well as 4,6-dinitro-2-phenylbenzo[b]furan, with various aminating agents were studied under the vicarious nucleophilic substitution conditions. It was found that depending on the aminating system, the starting compounds undergo either selective mono-amination at position 7 or double amination.

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References

  1. M. A. Bastrakov, A. M. Starosotnikov, A. Kh. Shakhnes, S. A. Shevelev, Russ. Chem. Bull., 2008, 57, 1539.

    Article  CAS  Google Scholar 

  2. P. F. Pagoria, A. R. Mitchell, R. D. Schmidt, J. Org. Chem., 1996, 61, 2934.

    Article  CAS  Google Scholar 

  3. M. Makosza, M. Bialecki, J. Org. Chem., 1998, 63, 4878.

    Article  CAS  Google Scholar 

  4. A. R. Katritzky, K. S. Laurenzo, J. Org. Chem., 1986, 51, 5039.

    Article  CAS  Google Scholar 

  5. S. Seko, K. Miyake, N. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1999, 1437.

    Google Scholar 

  6. J. Meisenheimer, E. Patzig, Chem. Ber., 1906, 39, 2533.

    Article  Google Scholar 

  7. H. Goldhahn, J. Parkt. Chem., 1940, 156, 315.

    Article  CAS  Google Scholar 

  8. R. P. Veltman, Zh. Obshch. Khim. [J. Gen. Chem. USSR], 1960, 30, 1363 (in Russian).

    CAS  Google Scholar 

  9. V. G. Pesin, A. M. Khaletskii, V. A. Sergeev, Zh. Obshch. Khim. [J. Gen. Chem. USSR], 1964, 34, 258 (in Russian).

    Google Scholar 

  10. A. Schmidt, Adv. Heterocycl. Chem., 2003, 85, 67.

    Article  CAS  Google Scholar 

  11. Atta-ur-Rahman, S. Malik, H. Cun-heng, J. Clardy, Tetrahedron Lett., 1985, 26, 2759.

    Article  CAS  Google Scholar 

  12. Y.-M. Liu, J.-S. Yang, Q.-H. Liu, Chem. Pharm. Bull., 2004, 52, 454.

    Article  CAS  Google Scholar 

  13. Atta-ur-Rahman, S. Malik, S. S. Hasan, M. I. Choudhary, C.-Z. Ni, J. Clardy, Tetrahedron Lett., 1995, 36, 1993.

    Article  CAS  Google Scholar 

  14. G. P. Sharnin, F. S. Levinson, S. A. Akimova, R. Kh. Khasanov, SU Pat. 745901, 1978.

    Google Scholar 

  15. W. P. Norris, US Pat. 5039812.

  16. A. M. Starosotnikov, A. V. Lobach, V. V. Kachala, S. A. Shevelev, Russ. Chem. Bull., 2004, 53, 584.

    Article  CAS  Google Scholar 

  17. D. A. Brovko, V. N. Marshalkin, V. V. Semenov, Chem. Heterocycl. Compd., 2001, 37, 504.

    Article  CAS  Google Scholar 

  18. M. D. Dutov, I. A. Vatsadze, S. S. Vorob´ev, S. A. Shevelev, Mendeleev Commun., 2005, 15, 202.

    Article  Google Scholar 

  19. A. L. Spek, Acta Crystallogr. C, 2015, 71, 9.

    Article  CAS  Google Scholar 

  20. G. M. Sheldrick, Acta Crystallogr. A, 2015, 71, 3.

    Article  Google Scholar 

  21. G. M. Sheldrick, Acta Crystallogr. C, 2015, 71, 3.

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. M. Starosotnikov, M. A. Bastrakov, V. V. Kachala & S. A. Shevelev

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    I. V. Fedyanin

Authors
  1. A. M. Starosotnikov
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  2. M. A. Bastrakov
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  3. V. V. Kachala
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  4. I. V. Fedyanin
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  5. S. A. Shevelev
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Additional information

Deceased.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0390—0393, February, 2020.

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Starosotnikov, A.M., Bastrakov, M.A., Kachala, V.V. et al. Vicarious nucleophilic amination of five-membered 4,6-dinitrobenzoheterocycles. Russ Chem Bull 69, 390–393 (2020). https://doi.org/10.1007/s11172-020-2773-z

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  • DOI: https://doi.org/10.1007/s11172-020-2773-z

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