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Reactions of pyrazinium salts with phenols:from σH-adducts to SN Hproducts and transformations into benzo[b]furans

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Abstract

The reaction of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium salts with phenol derivatives affords relatively stable dihydropyrazines, whereas the reactions of 6-(het)aryl-1,2,5-oxadiazolo[3,4-b]pyrazin-4-ium protic salts, depending on the phenol structure, result in products of nucleophilic substitution of hydrogen or open-chain transformation products: benzo[b]furan-substituted derivatives. The crystallographic data on the spatial structure of all types of the synthesized products were obtained.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    E. V. Verbitskiy, Yu. A. Kvashnin, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin & V. N. Charushina

  2. Institute of Chemistry, Komi Research Center, Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167982, Syktyvkar, Russian Federation

    A. V. Kuchin

Authors
  1. E. V. Verbitskiy
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  2. Yu. A. Kvashnin
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  3. P. A. Slepukhin
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  4. A. V. Kuchin
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  5. G. L. Rusinov
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  6. O. N. Chupakhin
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  7. V. N. Charushina
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Correspondence to G. L. Rusinov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 898–906, May, 2011.

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Verbitskiy, E.V., Kvashnin, Y.A., Slepukhin, P.A. et al. Reactions of pyrazinium salts with phenols:from σH-adducts to SN Hproducts and transformations into benzo[b]furans. Russ Chem Bull 60, 919–928 (2011). https://doi.org/10.1007/s11172-011-0144-5

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  • DOI: https://doi.org/10.1007/s11172-011-0144-5

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