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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
Article
  • 53 Downloads

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.

Keywords

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

Notes

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

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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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