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Synthesis of polyfunctionalized 1,1'-(α,ω-alkanediyl)bis(1,2,3,4-tetrahydropyridines)

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Chemistry of Heterocyclic Compounds Aims and scope

A one-pot reaction was developed for the synthesis of polyfunctionalized 1,1'-(α,ω-alkanediyl)bis(1,2,3,4-tetrahydropyridines) in 28–69% yields on the basis of a three-component reaction between 1,3-dicarbonyl compounds, aqueous 33% solution of formaldehyde, and α,ω-diamines.

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References

  1. Misra, M.; Pandey, S. K.; Pandey, V. P.; Pandey, J.; Tripathi, R.; Tripathi, R. P. Bioorg. Med. Chem. 2009, 17, 625.

    Article  CAS  Google Scholar 

  2. Zhang, L.; Kim, C. U.; Xu, L. Tetrahedron Lett. 2007, 48, 3273.

    Article  CAS  Google Scholar 

  3. Aridoss, C.; Amirthaganesan, S.; Jeong, Y. T. Bioorg. Med. Chem. Lett. 2010, 20, 2242.

    Article  CAS  Google Scholar 

  4. Sun, Ch.-W.; Wang, J.; Wu, Y.; Nan, S.-B.; Zhang, W.-G. Heterocycles 2013, 87, 1865.

    Article  CAS  Google Scholar 

  5. Brown, B. S.; Keddy, R.; Zheng, G. Z.; Schmidt, R. G.; Koenig, J. R.; McDonald, H. A.; Bianchi, B. R.; Honore, P.; Jarvis, M. F.; Surowy, C. S.; Polakowski, J. S.; Marsh, K. C.; Faltynek, C. R.; Lee, C.-H. Bioorg. Med. Chem. 2008, 16, 8516.

    Article  CAS  Google Scholar 

  6. Leon, L. G.; Carballo, R. M.; Vega-Hernández, M. C.; Martín, V. S.; Padrón, J. I.; Padrón, J. M. Bioorg. Med. Chem. Lett. 2007, 17, 2681.

    Article  CAS  Google Scholar 

  7. (a) Malviya, M.; Sunil Kumar, Y. C.; Mythri, R. B.; Venkateshappa, C.; Subhash, M. N.; Rangappa, K. S. Bioorg. Med. Chem. 2009, 17, 5526. (b) Zheng, G.; Smith, A. M.; Huang, X.; Subramanian, K. L.; Siripurapu, K. B.; Deaciuc, A.; Zhan, Ch.-G.; Dwoskin, L. P. J. Med. Chem. 2013, 56, 1693.

  8. Ramachandran, P. V.; Burghardt, T. E.; Bland-Berry, L. J. Org. Chem. 2005, 70, 7911.

    Article  CAS  Google Scholar 

  9. (a) Suleman, N. K.; Flores, J.; Tanko, J. M.; Isin, E. M.; Castaglonoli, N. Bioorg. Med. Chem. 2008, 16, 8557. (b) Morale, M. C.; Serra, P. A.; L'episcopo, F.; Tirolo, C.; Caniglia, S.; Testa, N.; Gennuso, F.; Giaquinta, G.; Rocchitta, G.; Desole, M. S.; Miele, E.; Marchetti, B. Neuroscience 2006, 138, 869. (c) Kadieva, M. G.; Oganesyan, E. T.; Mutsueva, S. Kh. Pharm. Chem. J. 2005, 39, 453. (d) Xu, K.; Xu, Y.; BrownJermyn, D.; Chen, J. F.; Ascherio, A.; Dluzen, D. E.; Schwarschild, M. A. J. Neurosci. 2006, 26, 535.

  10. (a) Sridharan, V.; Maiti, S.; Menendez, J. C. Chem.–Eur. J. 2009, 15, 4565. (b) Han, R.-G.; Wang, Y.; Li, Y.-Y.; Xu, P.-F. Adv. Synth. Catal. 2008, 350, 1474. (c) Jiang, H.-F.; Li, J.-H.; Chen, Z.-W. Tetrahedron 2010, 66, 9721.

  11. Yu, D.-F.; Wang, Y.; Xu, P.-F. Tetrahedron 2011, 67, 3273.

    Article  CAS  Google Scholar 

  12. Verma, S.; Kumar, S.; Jain, S. L.; Sain, B. Org. Biomol. Chem. 2011, 9, 6943.

    Article  CAS  Google Scholar 

  13. Banfi, L.; Basso, A.; Lambruschini, Ch.; Moni, L.; Riva, R. Chem. Heterocycl. Compd. 2017, 53, 382. [Khim. Geterotsikl. Soedin. 2017, 53, 382.]

  14. Mehrabi, H.; Mohebbi, A. ARKIVOC 2016, (v), 89.

    Google Scholar 

  15. Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.

    Article  CAS  Google Scholar 

  16. Sperger, C. A.; Mayer, P.; Wanner, K. T. Tetrahedron 2009, 65, 10463.

    Article  CAS  Google Scholar 

  17. (a) Lee, H. K.; Im, J. H.; Jung, S. H. Tetrahedron 2007, 63, 3321. (b) Ishida, Y.; Hattori, K.; Yamamoto, H.; Iwashita, A.; Mihara, K.; Matsuoka, N. Bioorg. Med. Chem. Lett. 2005, 15, 4221. (c) Jansone, D.; Fleisher, M.; Andreeva, G.; Leite, L.; Lukevics, E. Chem. Heterocycl. Compd. 2005, 41, 1537. [Khim. Geterotsikl. Soedin. 2005, 1863.]

  18. (a) Harrison, T. J.; Dake, G. R. J. Org. Chem. 2005, 70, 10872. (b) Hernandez, F.; DelaCruz, F.; Lopez, J.; Pena, E.; Delgado, F.; Alcaraz, Y.; Robles, J.; Martinez-Alfaro, M.; Vazquez, M. A. J. Mex. Chem. Soc. 2014, 58, 152.

  19. Ishmiyarov, E. R.; Rakhimova, N. T.; Latypova, D. R.; Spirikhin, L. V.; Abdullin, M. I.; Dokichev, V. A. Russ. J. Org. Chem. 2015, 51, 1770. [Zh. Org. Khim. 2015, 51, 1803.]

  20. Latypova, D. R.; Badamshin, A. G.; Lobov, A. N.; Dokichev, V. A. Russ. J. Org. Chem. 2013, 49, 843 [Zh. Org. Khim. 2013, 49, 860.]

  21. Latypova, D. R.; Badamshin, A. G.; Gibadullina, N. N.; Khusnutdinova, N. S.; Zainullina, L. F.; Vakhitova, Yu. V.; Tomilov, Yu. V.; Dokichev, V. A. Med. Chem. Res. 2017, 26, 900.

  22. Reutov, O. A.; Butin, K. P.; Beletskaya, I. P. Russ. Chem. Rev. 1974, 43, 17. [Usp. Khim. 1974, 43, 35.]

  23. Komiyama, M.; Yoshinari, K. J. Org. Chem. 1997, 62, 2155.

    Article  CAS  Google Scholar 

  24. Zerov, A. V.; Krupenya, T. S.; Petrov, A. A.; Yakimovich, S. I. Russ. J. Org. Chem. 2016, 52, 312. [Zh. Org. Khim. 2016, 52, 332.]

  25. (a) Garbisch, E.; Griffith, M. G. J. Am. Chem. Soc. 1968, 90, 6543. (b) Günther, H. Course in NMR spectroscopy [Russian translation]; Mir: Moscow, 1984, p. 421.

  26. Saini, A.; Kumar, S.; Sandhu, J. S. J. Sci. Ind. Res. 2008, 67, 95.

    CAS  Google Scholar 

  27. Hantzsch, A. Chem. Ber. 1881, 14, 1637.

    Article  Google Scholar 

  28. Zheng, B. D.; Fulai, Y.; Wening, Z. CN Patent 101792412А.

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This work received financial support from the Russian Science Foundation (project No. 14-33-00022).

The spectral studies (NMR and mass spectra) were performed by using the equipment at Collective Use Center “Chemistry” at the Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave, Ufa, 450054, Russia

    Natalya N. Gibadullina, Dilara R. Latypova, Timur R. Nugumanov, Leonid V. Spirikhin & Vladimir A. Dokichev

  2. Ufa State Aviation Technical University, 12 Karla Marksa St, Ufa, 450008, Russia

    Vladimir A. Dokichev

Authors
  1. Natalya N. Gibadullina
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  2. Dilara R. Latypova
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  3. Timur R. Nugumanov
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  4. Leonid V. Spirikhin
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  5. Vladimir A. Dokichev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1098–1102

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Gibadullina, N.N., Latypova, D.R., Nugumanov, T.R. et al. Synthesis of polyfunctionalized 1,1'-(α,ω-alkanediyl)bis(1,2,3,4-tetrahydropyridines). Chem Heterocycl Comp 53, 1098–1102 (2017). https://doi.org/10.1007/s10593-017-2176-8

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  • DOI: https://doi.org/10.1007/s10593-017-2176-8

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