Advertisement

Chemistry of Heterocyclic Compounds

, Volume 54, Issue 11, pp 1050–1055 | Cite as

New transformations of N-hetarylcyclopentano[d][1,2,3]triazoline ring into 5-alkoxyvaleramidines

  • Nikolay A. Belyaev
  • Tetyana V. Beryozkina
  • Gert Lubec
  • Wim Dehaen
  • Vasiliy A. BakulevEmail author
REVIEW
  • 23 Downloads

It was found that brief refluxing of N-hetarylcyclopentano[d][1,2,3]triazolines in methanol resulted in the elimination of nitrogen, accompanied by cyclopentane ring opening with the formation of N-hetarylvaleramidines. Amidines containing pyrimidine-2,4-dione ring were synthesized by a one-step procedure – the reaction of 5-azidopyrimidine-2,4-diones with endocyclic enamines containing a cyclopentene ring proceeded through an N-pyrimidyl-1,2,3-triazoline intermediate. Triazolines containing a 1,3,5-triazine ring at position 1 did not form valeramidines upon refluxing in methanol. N-(1,3,5-triazin-2-yl)cyclopenta[d][1,2,3]triazoline containing a morpholine ring at position 6a underwent a different type of transformation upon dissolving in acetic acid, resulting in the formation of N-(1,3,5-triazin-2-yl)diaminoalkene. Mechanisms for these transformations are proposed.

Keywords

amidines imidazoles pyrimidinediones triazines triazolines ring transformations Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(11), 1050–1055 

Notes

This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 18-03-00715).

References

  1. 1.
    (a) Bakulev, V. A.; Beryozkina, T.; Thomas, J.; Dehaen, W. Eur. J. Org. Chem. 2018, 3, 262. (b) Burger, K.; Höß, E.; Sewald, N.; Geith, K.; Riede, J.; Bissinger, P. Z. Naturforsch. 1990, 45b, 1695. (c) Nikonov, I. L.; Kopchuk, D. S.; Kovalev, I. S.; Zyryanov, G. V.; Khasanov, A. F.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2013, 54, 6427.Google Scholar
  2. 2.
    (a) Bakulev, V. A.; Efimov, I. V.; Belyaev, N. A.; Rozin, Yu. A.; Volkova, N. N.; El'tsov, O. S. Chem. Heterocycl. Compd. 2012, 47, 1593. [Khim. Geterotsikl. Soedin. 2011, 47, 1900.] (b) Efimov, I.; Bakulev, V.; Beliaev, N.; Beryozkina, T.; Knippschild, U.; Leban, J.; Zhi-Jin, F.; Eltsov, O.; Slepukhin, P.; Ezhikova, M.; Dehaen, W. Eur. J. Org. Chem. 2014, 3684. a Efimov, I.; Beliaev, N.; Beryozkina, T.; Slepukhin, P.; Bakulev, V. Tetrahedron Lett. 2016, 57, 1949. b Adiche, C.; Hamadouche, M.; El Abed, D. Heterocycles 2016, 92, 1614.Google Scholar
  3. 3.
    Battistini, M.; Erba, E.; Pocar, D. J. Chem. Soc., Perkin Trans. 1 1993, 339.Google Scholar
  4. 4.
    Pocar, D.; Roversi, E.; Trimarco, P.; Valgattarri, G. Liebigs Ann. 1995, 487.Google Scholar
  5. 5.
    Erba, E.; Pokar, D.; Trimarco, P. J. Chem. Soc., Perkin Trans. 1 2001, 1723.Google Scholar
  6. 6.
    Erba, E.; Mai, G.; Pokar, D. J. Chem. Soc., Perkin Trans. 1 1992, 2709.Google Scholar
  7. 7.
    (a) Fusco, R.; Bianchetti, G.; Pokar, D. Gazz. Chim. Ital. 1961, 933. (b) Livi, O.; Amato, E.; Biagi, G.; Ferrarini, P. L.; Primofiore, G. P. Farmaco, Ed. Sci. 1978, 33, 838. (c) Nomura, Y.; Takeuchi, Y.; Tomoda, S.; Ito, M. M. Bull. Chem. Soc. Jpn. 1981, 54, 261. (d) Pocar, D.; Ripamonti, M. C; Stradi, R.; Trimarco, P. J. Heterocycl. Chem. 1977, 14, 173. (e) Xie, S.; Lopez, S. A.; Ramström, O.; Yan, M.; Houk, K. N. J. Am. Chem. Soc. 2015, 137, 2958. (f) Bertacche, V.; Contini, A.; Erba, E.; Nava, D.; Trimarco, P. Tetrahedron 2007, 63, 9652. (g) Beccalli, E. M.; Contini, A.; Trimarco, P. Tetrahedron 2005, 61, 4957. (h) Beccalli, E. M.; Contini, A.; Trimarco, P. Tetrahedron 2002, 58, 1213. (i) Julino, M.; Lowe, P. R.; Stevens, M. F. G. J. Chem. Res. 2000, 2, 74. (j) Mochul'skaya, N. N.; Nagibina, E. N.; Volchenkova, Yu. S.; Sidorova, L. P.; Charushin, V. N. Russ. J. Org. Chem. 2005, 41, 1694. [Zh. Org. Khim. 2005, 41, 1728.]Google Scholar
  8. 8.
    Ito, M. M.; Monura, Y.; Takeuchi, Y.; Tomoda, S. Bull. Chem. Soc. Jpn. 1983, 56, 641.CrossRefGoogle Scholar
  9. 9.
    (a) Stephen, J. F.; Marcus, E. J. Heterocycl. Chem. 1969, 969. (b) Contini, A.; Erba, E. RSC Adv. 2012, 2, 10652. (c) Pellegrino, S.; Contini, A.; Gelmi, M. L.; Presti L. L.; Soave, R.; Erba, E. J. Org. Chem. 2014, 79, 3094.Google Scholar
  10. 10.
    Beliaev, N. A.; Beryozkina, T. V.; Bakulev, V. A.; Lubec, G. Сhem. Heterocycl. Compd. 2018, 54, 984. [Khim. Geterotsikl. Soedin. 2018, 54, 984.]Google Scholar
  11. 11.
    Pocar, D.; Rossi, L. M.; Trimarco, P. J. Heterocycl. Chem. 1979, 16, 925.CrossRefGoogle Scholar
  12. 12.
    Xu, Y.; Wang, Y.; Zhu, S. J. Fluorine Chem. 2000, 104, 195.CrossRefGoogle Scholar
  13. 13.
    (a) Birney, D. M. Curr. Org. Chem. 2010, 14, 1658. (b) Bakulev, V. A. Russ. Chem. Rev. 1995, 64, 99. [Usp. Khim. 1995, 64, 107.]Google Scholar
  14. 14.
    Contini, A.; Erba, E.; Pellegrino, S. Synlett 2012, 1523.Google Scholar
  15. 15.
    (a) Beliaev, N. A.; Shafikov, M. Z.; Efimov, I. V.; Beryozkina, T. V.; Lubec, G.; Dehaen, W.; Bakulev, V. A. New. J. Chem. 2018, 42, 7049. (b) Wang, Z.; Wang, X.; Zhang, G.; Zhang, W.; Gao, Z. Chem. Lett. 2015, 44, 1333.Google Scholar
  16. 16.
    (a) Bhuyan, P. J.; Borah, H. N.; Sandhu, J. S. J. Chem. Soc., Perkin Trans. 1 1999, 3083. (b) Sako, M.; Ohara, S.; Hirota, K.; Kano, K.; Maki, Y.; Taylor, E. C. J. Org. Chem. 1991, 56, 6302.Google Scholar
  17. 17.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found Crystallogr. 2008, A64, 112.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nikolay A. Belyaev
    • 1
  • Tetyana V. Beryozkina
    • 1
  • Gert Lubec
    • 2
  • Wim Dehaen
    • 3
  • Vasiliy A. Bakulev
    • 1
    Email author
  1. 1.Department of Technology of Organic SynthesisUral Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Department of NeuroproteomicsParacelsus Medical UniversitySalzburgAustria
  3. 3.Laboratory of Molecular Design and Synthesis, Department of ChemistryCatholic University of LeuvenLeuvenBelgium

Personalised recommendations