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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. Chuvash State University named after I. N. Ulyanov, 15 Moskovsky Ave, Cheboksary, 428015, Russia

    Mikhail Yu. Belikov, Sergey V. Fedoseev, Mikhail Yu. Ievlev & Oleg V. Ershov

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  1. Mikhail Yu. Belikov
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  2. Sergey V. Fedoseev
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  3. Mikhail Yu. Ievlev
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  4. Oleg V. Ershov
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Correspondence to Mikhail Yu. Belikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 447–450

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Belikov, M.Y., Fedoseev, S.V., Ievlev, M.Y. et al. 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. Chem Heterocycl Comp 54, 447–450 (2018). https://doi.org/10.1007/s10593-018-2287-x

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  • DOI: https://doi.org/10.1007/s10593-018-2287-x

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