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ipso- and tele-Substitution in reactions of 3-chloro-1-ethyl-2-R-pyrazinium salts with C-nucleophiles

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Abstract

The reactions of 2,3-dichloro- and 3-chloro-1-ethyl-2-morpholinopyrazinium tetrafluoroborates with compounds containing the active methylene group were studied. The reactions with malonodinitrile and cyanoacetic ester afford products of ipso-substitution at position 2, while 1,3-dicarbonyl compounds produce products of tele-substitution of the Cl atom at the C(3) atom due to the attack of a nucleophile to position 6 of the pyrazine cycle.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, M. I. Kodess & O. N. Chupakhin

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. M. I. Kodess
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  5. O. N. Chupakhin
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Slepukhin, P.A., Rusinov, G.L., Charushin, V.N. et al. ipso- and tele-Substitution in reactions of 3-chloro-1-ethyl-2-R-pyrazinium salts with C-nucleophiles. Russian Chemical Bulletin 52, 689–694 (2003). https://doi.org/10.1023/A:1023919125480

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  • DOI: https://doi.org/10.1023/A:1023919125480

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