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Synthesis of 2,7-Diazabicyclo[3.2.1]oct-3-ene Derivatives

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Abstract

Tetracyanoethylene adducts with ketones, 4-oxoalkane-1,1,2,2-tetracarbonitriles reacted with hydrogen chloride or phosphorus(III) chloride in 1,4-dioxane to give 3-chloro-6-oxo-2,7-diazabicyclo[3.2.1]oct-3-ene-4,5-dicarbonitrile derivatives.

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References

  1. Barlocco, D., Cignarella, G., Tondi, D., Vianello, P., Villa, S., Bartolini, A., Ghelardini, C., Galeotti, N., Anderson, D.J., Kuntzweiler, T.A., Colombo, D., and Toma, L., J. Med. Chem., 1998, vol. 41, p. 674. doi https://doi.org/10.1021/jm970427p

    Article  CAS  PubMed  Google Scholar 

  2. Liu, H., Cheng, T.-M., Zhang, H.-M., and Li, R.-T., Arch. Pharm., 2003, vol. 336, p. 510. doi https://doi.org/10.1002/ardp.200300749

    Article  CAS  Google Scholar 

  3. Filosa, R., Peduto, A., de Caprariis, P., Saturnino, C., Festa, M., Petrella, A., Pau, A., Pinna, G.A., La Colla, P., Busonera, B., and Loddo, R., Eur. J. Med. Chem., 2007, vol. 42, p. 293. doi j.ejmech.2006.11.013.

    Article  CAS  PubMed  Google Scholar 

  4. Villa, S., Barlocco, D., Cignarella, G., Papp, G.P., Baláti, B., Takács, J., Varró, A., Borosy, A., Keserû, K., and Mátyus, P., Eur. J. Med. Chem., 2001, vol. 36, p. 495. doi https://doi.org/10.1016/S0223-5234(01)01246-6

    Article  CAS  PubMed  Google Scholar 

  5. Gordon, E.M., Duncton, M.A.J., and Gallop, M.A., J. Med. Chem., 2018, vol. 61, p. 10340. doi https://doi.org/10.1021/acs.jmedchem.8b01389

    Article  CAS  PubMed  Google Scholar 

  6. Dinsmore, C.J., Bergman, J.M., Bogusky, M.J., Culberson, J.C., Hamilton, K.A., and Graham, S.L., Org. Lett., 2001, vol. 3, p. 865. doi https://doi.org/10.1021/ol015504w

    Article  CAS  PubMed  Google Scholar 

  7. Kang, Z., Zhang, D., and Hu, W., Org. Lett., 2017, vol. 19, p. 3783. doi https://doi.org/10.1021/acs.orglett.7b01664

    Article  CAS  PubMed  Google Scholar 

  8. Marino, J.P., Kim, M.W., and Lawrence, R., J. Org. Chem., 1989, vol. 54, p. 1782. doi https://doi.org/10.1021/jo00269a004

    Article  CAS  Google Scholar 

  9. Inoue, K., Ishikawa, Y., and Nishiyama, S., Org. Lett., 2010, vol. 12, p. 436. doi https://doi.org/10.1021/o1902566p

    Article  CAS  PubMed  Google Scholar 

  10. Ershov, O.V., Ievlev, M.Yu., Belikov, M.Yu., and Nasakin, O.E., Russ. J. Org. Chem., 2016, vol. 52, p. 1353. doi https://doi.org/10.1134/S1070428016090189

    Article  CAS  Google Scholar 

  11. Ershov, O.V., Maksimova, V.N., Lipin, K.V., Belikov, M.Y., Ievlev, M.Y., Tafeenko, V.A., and Nasakin, O.E., Tetrahedron, 2015, vol. 71, p. 7445. doi https://doi.org/10.1016/j.tet.2015.06.031

    Article  CAS  Google Scholar 

  12. Kayukov, Y.S., Lukin, P.M., Nasakin, O.E., Khrustalev, V.N., Nesterov, V.N., Antipin, M.Y., and Lyshchikov, A.N., Chem. Heterocycl. Compd., 1997, vol. 33, p. 452. doi https://doi.org/10.1007/BF02321392

    Article  CAS  Google Scholar 

  13. Kayukov, Y.S., Lukin, P.M., Nasakin, O.E., Urman, Y.G., Khrustalev, V.N., Nesterov, V.N., Antipin, M.Y., and Sheverdov, V.V., Chem. Heterocycl. Compd., 1997, vol. 33, p. 457. doi https://doi.org/10.1007/BF02321393

    Article  CAS  Google Scholar 

  14. Nasakin, O.E., Sheverdov, V.P., Ershov, O.V., Moiseeva, I.V., Lyshchikov, A.N., Khrustalev, V.N., and Antipin, M.Y., Mendeleev Commun, 1997, vol. 7, p. 112. doi https://doi.org/10.1070/MC1997v007n03ABEH000722

    Article  Google Scholar 

  15. Lipin, K.V., Fedoseev, S.V., Ershov, O.V., and Tafeenko, V.A., Russ. J. Org. Chem., 2017, vol. 53, p. 1828. doi https://doi.org/10.1134/S1070428017120077

    Article  CAS  Google Scholar 

  16. Ershov, O.V., Lipin, K.V., Eremkin, A.V., Ershov, O.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 470. doi https://doi.org/10.1134/S1070428009030245

    Article  CAS  Google Scholar 

  17. Eremkin, A.V., Ershov, O.V., Lipin, K.V., Kayukov, Ya.S., Nasakin, O.E., and Tafeenko, V.A., Russ. J. Org. Chem., 2009, vol. 45, p. 1541. doi https://doi.org/10.1134/S1070428009100212

    Article  CAS  Google Scholar 

  18. Ershov, O.V., Lipin, K.V., Eremkin, A.V., Nasakin, O.E., Sheverdov, V.P., Fedorov, P.I., and Tafeenko, V.A., Russ. J. Org. Chem., 2017, vol. 53, p. 215. doi https://doi.org/10.1134/S1070428017020129

    Article  CAS  Google Scholar 

  19. Ershov, O.V., Ievlev, M.Y., Belikov, M.Y., Lipin, K.V., Naydenova, A.I., and Tafeenko, V.A., RSC Adv., 2016, vol. 6, p. 82227. doi https://doi.org/10.1039/C6RA16787J

    Article  CAS  Google Scholar 

  20. Lipin, K.V., Maksimova, V.N., Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2010, vol. 46, p. 617. doi https://doi.org/10.1134/S1070428017070120

    Article  CAS  Google Scholar 

  21. Belikov, M.Yu., Ievlev, M.Yu., Ershov, O.V., Lipin, K.V., Legotin, S.A., and Nasakin, O.E., Russ. J. Org. Chem., 2014, vol. 50, p. 1372. doi https://doi.org/10.1134/S1070428017050086

    Article  CAS  Google Scholar 

  22. Eremkin, A.V., Molkov, S.N., Ershov, O.V., Kayukov, Y.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Mendeleev Commun., 2006, vol. 16, p. 115. doi https://doi.org/10.1070/MC2006v016n02ABEH002206

    Article  CAS  Google Scholar 

  23. Ershov, O.V. and Ievlev, M.Y., Chem. Heterocycl. Compd., 2017, vol. 53, p. 948. doi https://doi.org/10.1007/s10593-017-2155-0

    Article  CAS  Google Scholar 

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Funding

This study was performed in the framework of the base part of state assignment of the Ministry of Science and Higher Education of the Russian Federation [project no. 4.6283.2017/8.9 (0849-2017-0001].

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Cheboksary, Russia

    O. V. Ershov, K. V. Lipin, M. Yu. Belikov & M. Yu. Ievlev

Authors
  1. O. V. Ershov
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  2. K. V. Lipin
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  3. M. Yu. Belikov
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  4. M. Yu. Ievlev
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Corresponding author

Correspondence to O. V. Ershov.

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Conflict of Interests

The authors declare no conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1115–1119.

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Ershov, O.V., Lipin, K.V., Belikov, M.Y. et al. Synthesis of 2,7-Diazabicyclo[3.2.1]oct-3-ene Derivatives. Russ J Org Chem 55, 1009–1012 (2019). https://doi.org/10.1134/S1070428019070170

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  • DOI: https://doi.org/10.1134/S1070428019070170

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