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Synthesis of 4-Halofuro[3,4-c]pyridin-3(1H)-ones from 2-Halopyridine-3,4-dicarbonitriles

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Abstract

Heating of 2-halopyridine-3,4-dicarboxylic acids in propionic anhydride led to the formation of 4-halofuro[3,4-c]pyridine-1,3-diones as a result of intramolecular dehydration of the vicinal carboxy groups. The subsequent reduction of 4-halofuro[3,4-c]pyridine-1,3-diones with sodium tetrahydridoborate in THF at room temperature afforded 4-halofuro[3,4-c]pyridin-3(1H)-ones as the major products.

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Funding

This study was performed under financial support by the President of the Russian Federation [program for state support of young Russian scientists, project no. 075-15-2020-229 (MK-269.2020.3)].

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, 428015, Cheboksary, Russia

    S. V. Fedoseev, M. Yu. Belikov & O. V. Ershov

  2. Faculty of Chemistry, Moscow State University, 119992, Moscow, Russia

    V. A. Tafeenko

Authors
  1. S. V. Fedoseev
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  2. M. Yu. Belikov
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  3. O. V. Ershov
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  4. V. A. Tafeenko
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Correspondence to S. V. Fedoseev.

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Fedoseev, S.V., Belikov, M.Y., Ershov, O.V. et al. Synthesis of 4-Halofuro[3,4-c]pyridin-3(1H)-ones from 2-Halopyridine-3,4-dicarbonitriles. Russ J Org Chem 56, 1540–1544 (2020). https://doi.org/10.1134/S1070428020090067

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  • DOI: https://doi.org/10.1134/S1070428020090067

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