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N → N acyl group migration in N-acylpyrazoles: Isomerization of 1,4-diacyl-5-methyl-1H-pyrazoles to 1,4-diacyl-3-methyl-1H-pyrazoles

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Abstract

1,4-Diacyl-5-methyl-1H-pyrazoles on heating in toluene undergo isomerization to 1,4-diacyl-3-methyl-1H-pyrazoles via intermolecular N → N acyl group migration. 1,4,5-Trisubstituted pyrazoles obtained by reaction of 2-ethoxymethylidene derivatives of 1,3-diketones with 1,3-benzothiazol-2-ylhydrazine or phenylhydrazine failed to isomerize to 1,3,4-trisubstituted pyrazoles.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg, 199034, Russia

    A. A. Petrov, V. V. Pakal’nis, A. V. Zerov & S. I. Yakimovich

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  1. A. A. Petrov
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  2. V. V. Pakal’nis
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  3. A. V. Zerov
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  4. S. I. Yakimovich
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Correspondence to A. A. Petrov.

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Original Russian Text © A.A. Petrov, V.V. Pakal’nis, A.V. Zerov, S.I. Yakimovich, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 3, pp. 384–394.

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Petrov, A.A., Pakal’nis, V.V., Zerov, A.V. et al. N → N acyl group migration in N-acylpyrazoles: Isomerization of 1,4-diacyl-5-methyl-1H-pyrazoles to 1,4-diacyl-3-methyl-1H-pyrazoles. Russ J Org Chem 53, 381–392 (2017). https://doi.org/10.1134/S1070428017030125

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  • DOI: https://doi.org/10.1134/S1070428017030125

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