Advertisement

Chemistry of Heterocyclic Compounds

, Volume 53, Issue 9, pp 1057–1060 | Cite as

Rearrangement of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the directed synthesis of aryl-substituted 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles

  • Mikhail Yu. BelikovEmail author
  • Sergey V. Fedoseev
  • Mikhail Yu. Ievlev
  • Oleg V. Ershov
Article

3-Aryl-4-oxoalkane-1,1,2,2-tetracarbonitriles were synthesized by the interaction of 2-aryl ketones with tetracyanoethylene. Directed rearrangement of them in acetic acid in the presence of ammonium acetate led to the formation of 2-(3-cyano-5-hydroxy-1,5-dihydro-2Hpyrrol-2-ylidene)malononitriles containing an aryl substituent in conjugation with the acceptor buta-1,3-diene-1,1,3-tricarbonitrile moiety.

Keywords

2-aryl ketones buta-1,3-diene-1,1,3-tricarbonitrile moiety 4-oxoalkane-1,1,2,2-tetracarbonitriles tetracyanoethylene rearrangement 

Notes

The study was carried out with the financial support of the Russian Foundation for Basic Research (project no 16-33-60156 mol_a_dk).

References

  1. 1.
    Li, H.; Zhao, P.; Zou, N.; Wang, H.; Sun, K. Tetrahedron Lett. 2017, 58, 30.CrossRefGoogle Scholar
  2. 2.
    Chen, T.; Zheng, Y.; Xu, Z.; Zhao, M.; Xu, Y.; Cui, J. Tetrahedron Lett. 2013, 54, 2980.CrossRefGoogle Scholar
  3. 3.
    Kim, S.-H.; Lee, S.-Y.; Gwon, S.-Y.; Bae, J.-S.; Son, Y.-A. J. Photochem. Photobiol., A 2011, 217, 224.Google Scholar
  4. 4.
    Lin, W.; Cui, Y.; Yu, J.; Yang, Y.; Qian, G. Dyes Pigm. 2017, 136, 791.CrossRefGoogle Scholar
  5. 5.
    Yang, Y.; Liu, J.; Xiao, H.; Zhen, Z.; Bo, S. Dyes Pigm. 2017, 139, 239.CrossRefGoogle Scholar
  6. 6.
    Malytskyi, V.; Simon, J.-J.; Patrone, L.; Raimundo, J.-M. RSC Adv. 2015, 5, 354.CrossRefGoogle Scholar
  7. 7.
    Cho, M. J.; Seo, J.; Oh, H. S.; Jee, H.; Kim, W. J.; Kim, K. H.; Hoang, M. H.; Choi, D. H.; Prasad, P. N. Sol. Energy Mater. Sol. Cells 2012, 98, 71.Google Scholar
  8. 8.
    Sharipova, S. M.; Kalinin, A. A. Chem. Heterocycl. Compd. 2017, 53, 36. [Khim. Geterotsikl. Soedin. 2017, 53, 36.]Google Scholar
  9. 9.
    Hao, Y.; Wood, C. J.; Clark, C. A.; Calladine, J. A.; Horvath, R.; Hanson-Heine, M. W. D.; Sun, X.-Z.; Clark, I. P.; Towrie, M.; George, M. W.; Yang, X.; Sun, L.; Gibson, E. A. Dalton Trans. 2016, 45, 7708.CrossRefGoogle Scholar
  10. 10.
    Liu, J.; Gao, W.; Kityk, I. V.; Liu, X.; Zhen, Z. Dyes Pigm. 2015, 122, 74.CrossRefGoogle Scholar
  11. 11.
    Huang, H.; Liu, J.; Zhen, Z.; Qiu, L.; Liu, X.; Lakshminarayana, G.; Tkaczyk, S.; Kityk, I. V. Mater. Lett. 2012, 75, 233.CrossRefGoogle Scholar
  12. 12.
    Deng, G.; Huang, H.; Si, P.; Xu, H.; Liu, J.; Bo, S.; Liu, X.; Zhen, Z.; Qiu, L. Polymer 2013, 54, 6349.CrossRefGoogle Scholar
  13. 13.
    Ipuy, M.; Liao, Y.-Y.; Jeanneau, E.; Baldeck, P. L.; Bretonnière, Y.; Andraud, C. J. Mater. Chem. C 2016, 4, 766.CrossRefGoogle Scholar
  14. 14.
    Belikov, M. Yu.; Fedoseev, S. V.; Ershov, O. V.; Ievlev, M. Yu.; Tafeenko, V. A. Tetrahedron Lett. 2016, 57, 4101.CrossRefGoogle Scholar
  15. 15.
    Ducker, J. W.; Gunter, M. J. Aust. J. Chem. 1973, 26, 1551.CrossRefGoogle Scholar
  16. 16.
    Fedoseev, S. V.; Belikov, M. Yu.; Ershov, O. V.; Bardasov, I. N.; Tafeenko, V. A. Russ. J. Org. Chem. 2016, 52, 1440. [Zh. Org. Khim. 2016, 52, 1450.].Google Scholar
  17. 17.
    Howard, G. E., Jr. US Patent 3178448; Chem. Abstr. 1965, 63, 713b.Google Scholar
  18. 18.
    Lu, Z.; Liu, N.; Lord, S. J.; Bunge, S. D.; Moerner, W. E.; Twieg, R. J. Chem. Mater. 2009, 21, 797.CrossRefGoogle Scholar
  19. 19.
    Lord, S.J.; Conley, N. R.; Lee, H.-I. D.; Nishimura, S. Y.; Pomerantz, A. K.; Willets, K. A.; Lu, Z.; Wang, H.; Liu, N.; Samuel, R.; Weber, R.; Semyonov, A.; He, M.; Twieg, R. J.; Moerner, W. E. ChemPhysChem 2009, 10, 55.CrossRefGoogle Scholar
  20. 20.
    Belikov, M. Yu.; Ievlev, M. Yu.; Ershov, O. V.; Lipin, K. V.; Legotin, S. A; Nasakin, O. E. Russ. J. Org. Chem. 2014, 50, 1372. [Zh. Org. Khim. 2014, 50, 1387.]Google Scholar
  21. 21.
    Belikov, M. Yu.; Ievlev, M. Yu.; Belikova, I. V.; Ershov, O. V.; Tafeenko, V. A.; Surazhskaya, M. D. Chem. Heterocycl. Compd. 2015, 51, 518. [Khim. Geterotsikl. Soedin. 2015, 51, 518.]Google Scholar
  22. 22.
    Ershov, O. V.; Ievlev, M. Yu.; Belikov, M. Yu.; Nasakin, O. E. Russ. J. Org. Chem. 2016, 52, 1353. [Zh. Org. Khim. 2016, 52, 1364.]Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Mikhail Yu. Belikov
    • 1
    Email author
  • Sergey V. Fedoseev
    • 1
  • Mikhail Yu. Ievlev
    • 1
  • Oleg V. Ershov
    • 1
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia

Personalised recommendations