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1-Aryl-5-carboxymethylhydantoin derivatives. structure of 1-phenyl-2-thio-5-carbomethoxymethylhydantoin

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of aromatic amines with maleic acid or its diethyl ester with subsequent hydrolysis gave N-arylaspartic acids, which were converted to 1-aryl- and 1-aryl-2-thio-5-carboxymethylhydantoins by the action of urea, cyanates, or thiocyanates in an acidic medium. Esterification of the acid products with methanol gave the corresponding carbomethoxymethylhydantoins, which were converted by reduction to tetrahydroimidazole derivatives and by acetylation to acetyl derivatives. Alkylation of the carboxymethylhydantoins with dimethyl sulfate gave 3-methyl derivatives of hydantoins, while alkylation with formaldehyde gave 3-hydroxymethyl derivatives of hydantoins. Data from the x-ray diffraction analysis of 1-phenyl-2-thio-5-carbomethoxymethylhydantoin are presented.

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Authors and Affiliations

  1. A. Snekchus Kaunas Polytechnic Institute, 233006, Kaunas

    R. S. Baltrushis, Z. -I. G. Beresnevichyus, I. M. Vizgaitis & Yu. V. Gatilov

  2. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 630090, Novosibirsk

    R. S. Baltrushis, Z. -I. G. Beresnevichyus, I. M. Vizgaitis & Yu. V. Gatilov

Authors
  1. R. S. Baltrushis
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  2. Z. -I. G. Beresnevichyus
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  3. I. M. Vizgaitis
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  4. Yu. V. Gatilov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1669–1674, December, 1981.

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Baltrushis, R.S., Beresnevichyus, Z.I.G., Vizgaitis, I.M. et al. 1-Aryl-5-carboxymethylhydantoin derivatives. structure of 1-phenyl-2-thio-5-carbomethoxymethylhydantoin. Chem Heterocycl Compd 17, 1226–1231 (1981). https://doi.org/10.1007/BF00506999

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  • DOI: https://doi.org/10.1007/BF00506999

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