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Reaction of 4,6-Di-tert-butyl-3-nitrocyclohexa-3,5-diene-1,2-dione with Secondary Amines

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Abstract

The reaction of 4,6-di-tert-butyl-3-nitrocyclohexa-3,5-diene-1,2-dione with secondary amines (piperidine, morpholine, 1-methylpiperazine) in isopropanol involves Michael addition and ANRORC and forms a mixture of products. The resulting compounds were characterized by IR and 1H and 13C NMR spectroscopy, and elemental analysis. The molecular structures of 3-nitrocyclohexa-3-ene-1,2-dione and cyclopenta-1,3-diene derivatives were established by X-ray diffraction analysis.

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CONFLICT OF INTEREST

The authors declare no conflict of interest.

REFERENCES

  1. Yang, J., Cohen Stuart, M.A., and Kamperman, M., Chem. Soc. Rev., 2014, vol. 43, p. 8271. https://doi.org/10.1039/C4CS00185K

    Article  CAS  PubMed  Google Scholar 

  2. Bruins, J.J., Albada, B., and van Delft, F.L., Chem. Eur. J., 2018, vol. 24, p. 4749. https://doi.org/10.1002/chem.201703919

    Article  CAS  PubMed  Google Scholar 

  3. Abakumov, G.A., Cherkasov, V.K., Kocherova, T.N., Druzhkov, N.O., Kurskii, Y.A., and Abakumova, L.G., Russ. Chem. Bull., 2006, vol. 55, p. 1195. https://doi.org/10.1007/s11172-006-0398-5

    Article  CAS  Google Scholar 

  4. Abakumov, G.A., Cherkasov, V.K., Kocherova, T.N., Druzhkov, N.O., Kurskii, Y.A., Bubnov, M.P., Fukin, G.K., and Abakumova, L.G., Russ. Chem. Bull., 2007, vol. 56, p. 1849. https://doi.org/10.1007/s11172-007-0287-6

    Article  CAS  Google Scholar 

  5. Abakumov, G.A., Druzhkov, N.O., Kurskii, Y.A., and Shavyrin, A.S., Russ Chem Bull., 2003, vol. 52, p. 712. https://doi.org/10.1023/A:1023979311368

    Article  CAS  Google Scholar 

  6. Abakumov, G.A., Druzhkov, N.O., Kurskii, Y.A., Abakumova, L.G., Shavyrin, A.S., Fukin, G.K., Poddel’skii, A.I., and Okhlopkova, L.S., Russ. Chem. Bull., 2005, vol. 54, p. 2571. https://doi.org/10.1007/s11172-006-0157-7

    Article  CAS  Google Scholar 

  7. Vinsova, J., Horak, V., Buchta, V., and Kaustova, J., Molecules, 2005, vol. 10, p. 783. https://doi.org/10.3390/10070783

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Vasu, D., Leitch, J.A., and Dixon, D.J., Tetrahedron, 2019, vol. 75, p. 130726. https://doi.org/10.1016/j.tet.2019.130726

    Article  CAS  Google Scholar 

  9. Ivakhnenko, E., Romanenko, G., Kovalenko, A., Revinskii, Yu., Knyazev, P., Kuzmin, V., and Minkin, V., Dyes Pigm., 2018, vol. 150, p. 97. https://doi.org/10.1016/j.dyepig.2017.11.009

    Article  CAS  Google Scholar 

  10. Cherkasov, V., Druzhkov, N., Kocherova, T., Fukin, G., and Shavyrin, A., Tetrahedron, 2011, vol. 67, p. 80. https://doi.org/10.1016/j.tet.2010.11.030

    Article  CAS  Google Scholar 

  11. Ivakhnenko, E., Malay, V., Romanenko, G., Demidov, O., Knyazev, P., Starikov, A., and Minkin, V., Tetrahedron, 2021, vol. 79, p. 131841. https://doi.org/10.1016/j.tet.2020.131841

    Article  CAS  Google Scholar 

  12. Ivakhnenko, E., Malay, V., Demidov, O., Starikov, A., and Minkin, V., Tetrahedron, 2022, vol. 103, p. 132575. https://doi.org/10.1016/j.tet.2021.132575

    Article  CAS  Google Scholar 

  13. Bhattacharya, S., Gupta, P., Basuli, F., and Pierpont, C.G., Inorg. Chem., 2002, vol. 41, p. 5810. https://doi.org/10.1021/ic025766+

    Article  CAS  PubMed  Google Scholar 

  14. CrysAlisPro, version 1.171.38.41, Rigaku Oxford Diffraction. 2015.

  15. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  16. Ley, K., Müller, E., Ley, K., and Müller, E., Chem. Ber., 1956, vol. 89, p. 1402.

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Science Foundation (project no. 19-13-00022; https://rscf.ru/project/19-13-00022/).

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Authors and Affiliations

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

    E. P. Ivakhnenko, V. I. Malai & V. I. Minkin

  2. North Caucasus Federal University, 355029, Stavropol, Russia

    O. P. Demidov

Authors
  1. E. P. Ivakhnenko
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  2. V. I. Malai
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  3. O. P. Demidov
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  4. V. I. Minkin
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Corresponding authors

Correspondence to E. P. Ivakhnenko or O. P. Demidov.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 8, pp. 1032–1040 https://doi.org/10.31857/S0514749223080049.

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Ivakhnenko, E.P., Malai, V.I., Demidov, O.P. et al. Reaction of 4,6-Di-tert-butyl-3-nitrocyclohexa-3,5-diene-1,2-dione with Secondary Amines. Russ J Org Chem 59, 1315–1321 (2023). https://doi.org/10.1134/S1070428023080043

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