Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 447–450 | Cite as

New approach to the synthesis of 2,3-dihydrofuro[2,3-b]pyridine derivatives: double reduction and double heterocyclization of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles in the presence of sodium borohydride

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

The reaction of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles with an excess of sodium borohydride resulted in diastereoselective formation of 2,3-diaryl-substituted 4,6-diamino-2,3-dihydrofuro[2,3-b]pyridine-5-carbonitriles. This process was accompanied by opening of the pyrrole ring in the starting compounds, followed by a double reduction and tandem closure of furan and pyridine rings.


2,3-dihydrofuro[2,3-b]pyridines sodium borohydride diastereoselectivity reduction 


The reported study was funded by the Russian Foundation for Basic Research (according to the research project No. 16-33-60156 mol_a_dk).


  1. 1.
    Fitch, R. W.; Spande, T. F.; Garraffo, H. M.; Yeh, H. J. C; Daly, J. W. J. Nat. Prod. 2010, 73, 331.CrossRefPubMedPubMedCentralGoogle Scholar
  2. 2.
    Zhou, Q.; Snider, B. B. Org. Lett. 2011, 13, 526.CrossRefPubMedGoogle Scholar
  3. 3.
    Gordon, J. C.; Phillips, E.; Gurley, D. A.; Heys, J. R.; Lazor, L. A.; Barthlow, H. G.; Mallamaci, M. A.; Keith, R. A. Eur. J. Pharmacol. 2010, 645, 63.CrossRefPubMedGoogle Scholar
  4. 4.
    Koike, T.; Hoashi, Y.; Takai, T.; Uchikawa, O. Tetrahedron Lett. 2011, 52, 3009.CrossRefGoogle Scholar
  5. 5.
    Elmore, C. S.; Landvatter, S.; Dorff, P. N.; Powell, M. E.; Killick, D.; Blake, T.; Hall, J.; Heys, J. R.; Harding, J.; Urbanek, R.; Ernst, G. J. Labelled Compd. Radiopharm. 2014, 57, 342.CrossRefGoogle Scholar
  6. 6.
    Bardasov, I. N.; Alekseeva, A. U.; Ershov, O. V.; Belikov, M. Yu. Tetrahedron Lett. 2015, 56, 5434.CrossRefGoogle Scholar
  7. 7.
    Alekseeva, A. Yu.; Bardasov, I. N.; Mihailov, D. L.; Ershov, O. V. Russ. J. Org. Chem. 2017, 53, 1243. [Zh. Org. Khim. 2017, 53, 1227.]Google Scholar
  8. 8.
    Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Grishanov, D. A. Tetrahedron Lett. 2015, 56, 1830.CrossRefGoogle Scholar
  9. 9.
    Ducker, J. W.; Williams, B. K. Aust. J. Chem. 1978, 31, 2327.CrossRefGoogle Scholar
  10. 10.
    Belikov, M. Yu.; Fedoseev, S. V.; Ievlev, M. Yu.; Ershov, O. V. Chem. Heterocycl. Compd. 2017, 53, 1057. [Khim. Geterotsikl. Soedin. 2017, 53, 1057.]Google Scholar
  11. 11.
    Belikov, M. Yu.; Fedoseev, S. V.; Ershov, O. V.; Ievlev, M. Yu.; Tafeenko, V. A. Tetrahedron Lett. 2016, 57, 4101.CrossRefGoogle Scholar
  12. 12.
    Zhu, D.; Ma, J.; Luo, K.; Fu, H.; Zhang, L.; Zhu, S. Angew. Chem. 2016, 128, 8592.CrossRefGoogle Scholar
  13. 13.
    Zhang, J.; Zhang, J.; Kang, Y.; Shi, J.; Yao, C. Synlett 2016, 1587.Google Scholar
  14. 14.
    Kojima, T.; Kawajiri, I.; Nishida, J.-i.; Kitamura, C.; Kurata, H.; Tanaka, M.; Ikeda, H.; Kawase, T. Bull. Chem. Soc. Jpn. 2016, 89, 931.CrossRefGoogle Scholar
  15. 15.
    Saleeb, M.; Mojica, S.; Eriksson, A.; Andersson, C. D.; Gylfe, Å.; Elofsson, M. Eur. J. Med. Chem. 2018, 143, 1077.CrossRefPubMedGoogle Scholar
  16. 16.
    Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700.CrossRefGoogle Scholar

Copyright information

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

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

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