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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 209–212 | Cite as

Selectivity in domino reaction of ortho-carbonyl azides with malononitrile dimer leading to [1,2,3]triazolo[1,5-a]pyrimidines

  • Nazariy T. Pokhodylo
  • Olga Ya. Shyyka
  • Mykola A. Tupychak
  • Mykola D. Obushak
Article
  • 66 Downloads

The selectivity of the domino reaction of the (het)aryl azides, containing the carbonyl center in the ortho position to the azido group, with malonodinitrile dimer was studied. It has been shown that in the case of aromatic azides bearing a carboxy or nitrile function in the ortho position, the reaction occurred with the formation of exclusively [1,2,3]triazolo[1,5-a]pyrimidine instead of [1,2,3]triazolo[4,5-b]pyridine system. Thus, new [1,2,3]triazolo[1,5-a]quinazolines, thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine, and thieno[3,2-e][1,2,3]triazolo[1,5-a]-pyrimidines, having polyfunctional 1-amino-2,2-dicyanovinyl fragment, were prepared in short time in high yields.

Keywords

azides malononitrile dimer [1,2,3]triazolo[1,5-a]pyrimidines domino reaction selectivity 

Notes

The authors are grateful to the Ministry of Education and Science of Ukraine for financial support of this project (grant 0116U008067).

References

  1. 1.
    Bardasov, I. N.; Golubev, R. V.; Ershov, O. V.; Kayukov, Y. S.; Nasakin, O. E. Tetrahedron Lett. 2011, 52, 4724.CrossRefGoogle Scholar
  2. 2.
    Bardasov, I. N.; Mikhailov, D. L.; Alekseeva, A. U.; Ershov, O. V.; Tafeenko, V. A. Tetrahedron Lett. 2016, 57, 2772.CrossRefGoogle Scholar
  3. 3.
    Zhang, W.; Wang, J.; Mao, J.; Hu, L.; Wu, X.; Guo, C. Tetrahedron Lett. 2016, 57, 1985.CrossRefGoogle Scholar
  4. 4.
    (a) Shaabani, A.; Hooshmand, S. E.; Tabatabaei, A. T. Tetrahedron Lett. 2016, 57, 351. (b) Al-Duaij, O. K.; Zaki, M. E. A.; El Gazzar, A.-R. B. A. Molecules 2016, 21, 1646. (c) Sun, F.; Zhu, F.; Shao, X.; Li, Z. Synlett 2015, 2306. (d) Li, J.; Yu, Y.; Tu, M.-S.; Jiang, B.; Wang, S.-L.; Tu, S.-J. Org. Biomol. Chem. 2012, 10, 5361.Google Scholar
  5. 5.
    (a) Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Grishanov, D. A. Tetrahedron Lett. 2015, 56, 1830. (b) Vereshchagin, A. N.; Elinson, M. N.; Anisina, Y. E.; Ryzhkov, F. V.; Goloveshkin, A. S.; Bushmarinov, I. S.; Zlotin, S. G.; Egorov, M. P. Mendeleev Commun. 2015, 25, 424. (c) Tu, X.-J.; Fan, W.; Hao, W.-J.; Jiang, B.; Tu, S.-J. ACS Comb. Sci. 2014, 16, 647.Google Scholar
  6. 6.
    Abbas, H.-A. S.; Abd El-Karim, S. S.; Ahmed, E. M.; Eweas, A. F.; El-Awdan, S. A. Acta Pol. Pharm. 2016, 73, 1163.Google Scholar
  7. 7.
    Tverdokhleb, N. M.; Khoroshilov, G. E.; Dotsenko, V. V. Tetrahedron Lett. 2014, 55, 6593.CrossRefGoogle Scholar
  8. 8.
    Pokhodylo, N. T.; Shyyka, O. Ya. Synth. Commun. 2017, 47, 1096.CrossRefGoogle Scholar
  9. 9.
    (а) Pokhodylo, N. T.; Shyyka, O. Ya.; Obushak, M. D. Synth. Commun. 2014, 44, 1002. (b) Pokhodylo, N. T.; Matiychuk, V. S. J. Heterocycl. Chem. 2010, 47, 415. (c) Pokhodylo, N. T.; Shyyka, O. Ya.; Savka, R. D.; Obushak, M. D. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2092. (d) Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Tetrahedron 2009, 65, 2678. (e) Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. Chem. Heterocycl. Compd. 2009, 45, 881. [Khim. Geterotsikl. Soedin. 2009, 1100.]Google Scholar

Copyright information

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

Authors and Affiliations

  • Nazariy T. Pokhodylo
    • 1
  • Olga Ya. Shyyka
    • 1
  • Mykola A. Tupychak
    • 1
  • Mykola D. Obushak
    • 1
  1. 1.Ivan Franko National University of LvivLvivUkraine

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