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Synthesis of 2-ethoxyprop-2-enal dimethylhydrazone and its Diels-Alder reactions

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Abstract

Conditions were found for the preparation of 2-ethoxyprop-2-enal dimethylhydrazone by reaction of 2-ethoxypropenal with N,N-dimethylhydrazine. 2-Ethoxyprop-2-enal dimethylhydrazone reacted with methyl vinyl ketone and methyl acrylate according to the [4 + 2]-cycloaddition pattern with regioselective formation of substituted tetrahydropyridines. The major product in the reaction of 2-ethoxyprop-2-enal dimethylhydrazone with 1,4-benzoquinone was 5-hydroxy-1-benzofuran-2-carbaldehyde dimethylhydrazone formed as a result of [3 + 2]-cycloaddition; a small amount of the corresponding [4 + 2]-cycloaddition product was also obtained. Some spontaneous transformations of the primary cycloaddition products were revealed.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. A. Keiko, T. A. Kuznetsova, L. I. Larina, Yu. A. Chuvashev, T. A. Klepikova & L. V. Sherstyannikova

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  1. N. A. Keiko
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  2. T. A. Kuznetsova
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  3. L. I. Larina
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  4. Yu. A. Chuvashev
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  5. T. A. Klepikova
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  6. L. V. Sherstyannikova
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Additional information

Original Russian Text © N.A. Keiko, T.A. Kuznetsova, L.I. Larina, Yu.A. Chuvashev, T.A. Klepikova, L.V. Sherstyannikova, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 10, pp. 1439–1443.

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Keiko, N.A., Kuznetsova, T.A., Larina, L.I. et al. Synthesis of 2-ethoxyprop-2-enal dimethylhydrazone and its Diels-Alder reactions. Russ J Org Chem 42, 1421–1425 (2006). https://doi.org/10.1134/S1070428006100010

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  • DOI: https://doi.org/10.1134/S1070428006100010

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