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Multicomponent Synthesis of 1,3-Bis[(alkylsulfanyl)methyl]-1,3,5-triazinan-2-ones

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Abstract

Previously unknown 5-alkyl-1,3-bis[(alkylsulfanyl)methyl]-1,3,5-triazinan-2-ones have been syn­thesized by three-component condensation of available N,N′-bis[(alkylsulfanyl)methyl]ureas with formaldehyde and primary amines in ethanol in the presence of sodium hydroxide or triethylamine. A one-pot four-component procedure has been proposed for the synthesis of the title compounds via successive thiomethylation of urea with a mixture of formaldehyde and alkanethiol and cycloaminomethylation of intermediate N,N′-bis[(alkyl­sulfanyl)methyl]ureas with formaldehyde and alkylamine.

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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) and Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment no. AAAA-A119-119011790021-4.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

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

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  1. L. A. Baeva
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  2. L. F. Biktasheva
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  3. T. R. Nugumanov
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  4. A. A. Fatykhov
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Correspondence to L. A. Baeva.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1727–1735 https://doi.org/10.31857/S0514749221120077.

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Baeva, L.A., Biktasheva, L.F., Nugumanov, T.R. et al. Multicomponent Synthesis of 1,3-Bis[(alkylsulfanyl)methyl]-1,3,5-triazinan-2-ones. Russ J Org Chem 57, 1948–1954 (2021). https://doi.org/10.1134/S1070428021120071

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