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Synthesis of Ethyl 2-[Alkyl(benzyl)sulfanylmethyl]-3-oxobutanoates and 3H-Pyrazol-3-ones Based Thereon

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Abstract

Three-component condensation of ethyl acetoacetate with formaldehyde and alkanethiols in the presence of 0.1 equiv of sodium hydroxide afforded ethyl 2-[(alkylsulfanyl)methyl]-3-oxobutanoates, and analogous reaction with phenylmethanethiol led to the formation of ethyl 2-[(benzylsulfanyl)methyl]-2-(hydroxymethyl)-3-oxobutanoate. The condensation products reacted with hydrazine hydrate in ethanol at room temperature to give 4-{[alkyl(or benzyl)sulfanyl]methyl}-5-methyl-2,4-dihydro-3H-pyrazol-3-ones which were shown to exist in DMSO-d6 mainly as 1H-pyrazol-5(3)-ol tautomers.

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Acknowledgments

The spectral and analytical data were obtained using the equipment of the Chemistry Joint Center (Ufa Institute of Chemistry, Russian Academy of Sciences).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia

    L. A. Baeva, R. M. Nugumanov, L. F. Biktasheva, T. R. Nugumanov & A. A. Fatykhov

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  1. L. A. Baeva
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  2. R. M. Nugumanov
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  3. L. F. Biktasheva
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  4. T. R. Nugumanov
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  5. A. A. Fatykhov
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Corresponding author

Correspondence to L. A. Baeva.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 4, pp. 531–537.

Funding

This study was performed in the framework of state assignment (project nos. AAAA-A17-117011910030-0, AAAA-A17-117011910027-0).

Conflict of Interests

The authors declare the absence of conflict of interests.

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Baeva, L.A., Nugumanov, R.M., Biktasheva, L.F. et al. Synthesis of Ethyl 2-[Alkyl(benzyl)sulfanylmethyl]-3-oxobutanoates and 3H-Pyrazol-3-ones Based Thereon. Russ J Org Chem 55, 442–447 (2019). https://doi.org/10.1134/S1070428019040043

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  • DOI: https://doi.org/10.1134/S1070428019040043

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