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Conditions for the Selective Conversion of Quaternary 3-Anilino-1,5-dimethylpyrazolium Salts into 3-Anilino-1,5-dimethylpyrazole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The possibility has been studied of converting quaternary 3-anilino-1,5-dimethylpyrazolium salts into 3-anilino-1,5-dimethylpyrazole, the first representative of the 1-alkyl-3-arylaminopyrazoles. The dependence of the reaction direction on the nature of the substituent at position 2 has been clarified. The most effective result was obtained with a cyanoethyl substituent. On boiling the initial salt with aqueous ammonia the target product is isolated in quantitative yield. Syntheses of the initial salts are described. C-Sulfonation was detected on interacting 3-anilino-1-benzoyl-3-methylpyrazole and dimethyl sulfate, with the formation of p-(3-amino-1,2,5-trimethylpyrazolio)benzenesulfonate.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Kiev, 02094

    I. B. Dzvinchuk, S. A. Kartashov, A. V. Vypirailenko & M. O. Lozinskii

  2. Aventis CropScience Gmbh, D-65926, Frankfurt-on-Main, Germany

    U. Doller

Authors
  1. I. B. Dzvinchuk
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  2. S. A. Kartashov
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  3. A. V. Vypirailenko
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  4. U. Doller
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  5. M. O. Lozinskii
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Dzvinchuk, I.B., Kartashov, S.A., Vypirailenko, A.V. et al. Conditions for the Selective Conversion of Quaternary 3-Anilino-1,5-dimethylpyrazolium Salts into 3-Anilino-1,5-dimethylpyrazole. Chemistry of Heterocyclic Compounds 40, 570–574 (2004). https://doi.org/10.1023/B:COHC.0000037311.01960.3e

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  • DOI: https://doi.org/10.1023/B:COHC.0000037311.01960.3e

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