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Synthesis of new 5-substituted hydantoins from 2-alkoxy-1-cyano-1-trimethylsiloxypropenes

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Abstract

Synthetic procedures for preparing previously unknown 5-(1′-alkoxyethylidene)hydantoins from 2-alkoxy-1-cyano-1-trimethylsiloxy-1-(or -2-)propenes by one-pot successive reactions with ethanol and (NH4)2CO3 are developed. Some intermediates, reaction mechanism, and parameters determining the optimal yields are considered. Acid hydrolysis of ethylidenehydantoins occurs at the vinyloxy group and gives 5-acetylhydantoin in 64% yield.

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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, N. V. Vchislo, Yu. A. Chuvashev, L. I. Larina & M. G. Voronkov

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  1. N. A. Keiko
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  2. T. A. Kuznetsova
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  3. N. V. Vchislo
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  4. Yu. A. Chuvashev
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  5. L. I. Larina
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  6. M. G. Voronkov
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Correspondence to N. A. Keiko.

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Original Russian Text © N.A. Keiko, T.A. Kuznetsova, N.V. Vchislo, Yu.A. Chuvashev, L.I. Larina, M.G. Voronkov, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 12, pp. 2002–2006.

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Keiko, N.A., Kuznetsova, T.A., Vchislo, N.V. et al. Synthesis of new 5-substituted hydantoins from 2-alkoxy-1-cyano-1-trimethylsiloxypropenes. Russ J Gen Chem 77, 2145–2149 (2007). https://doi.org/10.1134/S1070363207120122

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  • DOI: https://doi.org/10.1134/S1070363207120122

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