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Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles

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Abstract

Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN—AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro-1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported.

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References

  1. V.N. Charushin, I.V. Kazantseva, M.G. Ponizovskii, L.G. Egorova, E.O. Sidorov, and O.N. Chupakhin, Khim. Geterotsikl.Soedin., 1986, 1380 [Chem.Heterocycl.Compd., 1986, 10 (Engl.Transl.)].

    Google Scholar 

  2. V.N. Charushin, M.G. Ponizovskii, O.N. Chupakhin, E.O. Sidorov, and I.M. Sosonkin, Khim.Geterotsikl.Soedin., 1985, 669 [Chem.Heterocycl.Compd., 1985 (Engl.Transl.)].

  3. J. Clark, J.Chem.Soc.(C), 1967, 1543.

  4. O.N. Chupakhin, V.N. Charushin, and A.R. Chernyshev, Progress in Nuclear Magnetic Resonance Spectroscopy, 1988, 20, pp95.

  5. T.J. Batterham, J.Chem.Soc.(C), 1969, 999.

  6. G.B. Barlin, The Pyrazines, Wiley Interscience, New York, 1982.

    Google Scholar 

  7. G.L. Rusinov, P.A. Slepukhin, V.N. Charushin, and O.N. Chupakhin, Mendeleev.Commun., 2001, 2, pp78.

    Google Scholar 

  8. H. Hirano, R. Lee, and M. Tada, J.Heterocyclic Chem., 1982, 1409.

  9. P.J. Brach, S.J. Grammatica, A.O. Ossanna, and L. Weinberger, J.Heterocyclic Chem., 1970, 1403.

  10. F.D. Popp, J.Heterocyclic Chem., 1974, 79.

  11. V.N. Charushin and O.N. Chupakhin, Heterocycles, 1981, 2, pp195.

    Google Scholar 

  12. V.I. Filyakova, N.S. Karpenko, O.A. Kuznetsova, and K.I. Pashkevich, Zh.Org.Khim., 1998, 34, pp411 [Russ.J.Org. Chem., 1998, 34 (Engl.Transl.)].

  13. A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo, Acta Crystallogr.(A), 1991, 47, pp74.

  14. L.H. Straver and A.J. Schierbeek, MOLEN.Structure De termination System, 1, Program Description, Nonius B.V., 1994, 180.

  15. A.L. Spek, Acta Crystalogr.(A), 1990, 46, pp34.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation, Russia

    P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, V. I. Filyakova & N. S. Karpenko

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation, Russia

    D. B. Krivolapov & I. A. Litvinov

Authors
  1. P. A. Slepukhin
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  2. G. L. Rusinov
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  3. V. N. Charushin
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  4. V. I. Filyakova
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  5. N. S. Karpenko
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  6. D. B. Krivolapov
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  7. I. A. Litvinov
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Slepukhin, P.A., Rusinov, G.L., Charushin, V.N. et al. Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles. Russian Chemical Bulletin 53, 1272–1278 (2004). https://doi.org/10.1023/B:RUCB.0000042286.61289.bf

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  • DOI: https://doi.org/10.1023/B:RUCB.0000042286.61289.bf

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