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Reduction of 3-carbonyl-substituted 5,6-dicyanobenzofurans with sodium borohydride

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Reduction of 3-R-carbonyl-substituted 5,6-dicyanobenzofurans with sodium borohydride was studied under various conditions. 3-R-Carbonyl-substituted 5,6-dicyanobenzofurans are selectively reduced in ethanol to substituted 3-R-(hydroxymethyl)-5,6-dicyano-2-methylbenzofurans, products of more deep reduction, viz., substituted 3-R-(hydroxymethyl)-2-methyl-2,3-dihydro-5,6-dicyanobenzofurans, 3-R-(hydroxymethyl)-5,6-dicyano-2-methylbenzofurans, and 3-alkyl-substituted 4-hydroxyphthalonitriles, are formed in tetrahydrofuran.

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Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii prosp., 150023, Yaroslavl, Russian Federation

    Zh. V. Chirkova, S. I. Filimonov & I. G. Abramov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    S. I. Firgang & G. A. Stashina

Authors
  1. Zh. V. Chirkova
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  2. S. I. Filimonov
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  3. I. G. Abramov
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  4. S. I. Firgang
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  5. G. A. Stashina
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Corresponding author

Correspondence to S. I. Filimonov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1693–1696, August, 2011.

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Chirkova, Z.V., Filimonov, S.I., Abramov, I.G. et al. Reduction of 3-carbonyl-substituted 5,6-dicyanobenzofurans with sodium borohydride. Russ Chem Bull 60, 1719–1722 (2011). https://doi.org/10.1007/s11172-011-0256-y

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  • DOI: https://doi.org/10.1007/s11172-011-0256-y

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