Advertisement

Chemistry of Heterocyclic Compounds

, Volume 52, Issue 4, pp 262–266 | Cite as

A domino reaction for the synthesis of 2H-pyrano-[4″,3″,2″:4′,5′]chromeno[2′,3′:4,5]thieno-[2,3-b]pyridin-2-ones

  • Svitlana P. Bondarenko
  • Igor V. Zhitnetskyi
  • Serhii V. Semenov
  • Mykhaylo S. Frasinyuk
Article
2-{[(5-Hydroxy-2-oxo-2H-chromen-4-yl)methyl]sulfanyl}pyridine-3-carbonitrile derivatives were synthesized in a reaction of 4-chloromethyl-5-hydroxycoumarin with substituted 2-thioxopyridine-3-carbonitriles. The presence in the molecule of spatially adjacent active methylene, nitrile, and hydroxyl groups under the action of a base leads to consecutive intramolecular cyclization reactions with the formation of a novel heterocyclic system pyrano[4″,3″,2″:4′,5′]chromeno[2′,3′:4,5]thieno[2,3-b]pyridine.

Keywords

4-chloromethylcoumarin 4-(3-cyanopyridin-2-yl-sulfanylmethyl)coumarin pyrano[4″,3″,2″:4′,5′]chromeno[2′,3′:4,5]thieno-[2,3-b]pyridine domino reaction intramolecular cyclization 

References

  1. 1.
    Manners, G. D.; Jurd, L.; Wong, R.; Palmer, K. Tetrahedron 1975, 31, 3019.CrossRefGoogle Scholar
  2. 2.
    Takashima, J.; Asano, S.; Ohsaki, A. Planta Med. 2002, 68, 621.CrossRefGoogle Scholar
  3. 3.
    Jassbi, A. R.; Singh, P.; Jain, S.; Tahara, S. Helv. Chim. Acta 2004, 87, 820.CrossRefGoogle Scholar
  4. 4.
    (a) He, J.; Silva, A. M. S.; Mateus, N.; de Freitas, V. Food Chem. 2011, 127, 984. (b) Blanco-Vega, D.; López-Bellido, F. J.; Alía-Robledo, J. M.; Hermosín-Gutiérrez, I. J. Agric. Food Chem. 2011, 59, 9523. (c) Oliveira, J.; Azevedo, J.; Silva, A. M. S.; Teixeira, N.; Cruz, L.; Mateus, N.; de Freitas, V. J. Agric. Food Chem. 2010, 58, 5154. (d) He, J.; Oliveira, J.; Silva, A. M. S.; Mateus, N.; De Freitas, V. J. Agric. Food Chem. 2010, 58, 8814.Google Scholar
  5. 5.
    (a) Westerlund, F.; Hildebrandt, C. B.; Sørensen, T. J.; Laursen, B. W. Chem.–Eur. J. 2010, 16, 2992. (b) Laursen, B. W.; Krebs, F. C. Chem.–Eur. J. 2001, 7, 1773. (s) Oliveira, J.; Mateus, N.; Rodriguez-Borges, J. E.; Cabrita, E. J.; Silva, A. M. S.; de Freitas, V. Tetrahedron Lett. 2011, 52, 2957.Google Scholar
  6. 6.
    Commandeur, C.; Florent, J.-C.; Rousselle, P., Bertounesque, E. Eur. J. Org. Chem. 2011, 1447.Google Scholar
  7. 7.
    Mazzei, M. E. A.; Balbi, A.; Di Braccio, M.; Schiantarelli, P.; Cadel, S. Farmaco 1986, 41, 611.Google Scholar
  8. 8.
    Jassbi, A. R.; Singh, P.; Lamba, J.; Jain, S.; Baldwin, I. T.; Tahara, S. Z. Naturforsch. 2006, 61b, 73.Google Scholar
  9. 9.
    Görlitzer, K.; Badia, G.; Jones, P. G. Pharmazie 2001, 401.Google Scholar
  10. 10.
    (a) Frasinyuk, M. S.; Gorelov, S. V.; Bondarenko, S. P.; Khilya, V. P. Chem. Heterocycl. Compd. 2009, 45, 1261. [Khim. Geterotsikl. Soedin. 2009, 1568.] (b) Khan, I. A.; Kulkarni, M. V.; Gopal, M.; Shahabuddin, M. S.; Sun, C. M. Bioorg. Med. Chem. Lett. 2005, 15, 3584.Google Scholar
  11. 11.
    Gorelov, S. V.; Bondarenko, S. P.; Frasinyuk, M. S. Chem. Heterocycl. Compd. 2012, 48, 955. [Khim. Geterotsikl. Soedin. 2012, 1026.]Google Scholar
  12. 12.
    Frasinyuk, M. S.; Bondarenko, S. P.; Sviripa, V. M.; Burikhanov, R.; Rangnekar, V. M.; Liu, C.; Watt, D. S. Tetrahedron Lett. 2015, 56, 3382.CrossRefGoogle Scholar
  13. 13.
    (a) Duddeck, H.; Kaiser, M. Org. Magn. Res. 1982, 20, 55. (b) Karami, B.; Kiani, M. J. Chin. Chem. Soc. 2014, 61, 213.Google Scholar
  14. 14.
    Valizadeh, H.; Shockravi, A. Tetrahedron Lett. 2005, 46, 3501.CrossRefGoogle Scholar
  15. 15.
    Frasinyuk, M. S.; Bondarenko, S. P.; Khilya, V. P. Chem. Heterocycl. Compd. 2009, 45, 290. [Khim. Geterotsikl. Soedin. 2009, 361.]Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Svitlana P. Bondarenko
    • 1
  • Igor V. Zhitnetskyi
    • 1
  • Serhii V. Semenov
    • 2
  • Mykhaylo S. Frasinyuk
    • 2
  1. 1.National University of Food TechnologiesKyivUkraine
  2. 2.Institute of Bioorganic Chemistry and PetrochemistryNational Academy of Sciences of UkraineKyivUkraine

Personalised recommendations