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Heterocyclic compounds based on maleic acid monoureide

1. Structure and transformations of the product of bromination of maleic acid monoureide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The products of the bromination in water of maleic acid monoureide and its methyl ester have the 2-imino-5-bromocarboxy(carbomethoxy)methyl-4-oxazolidone structure. 2-Imino-5-bromocarboxymethyl-4-oxazolidone undergoes dehydrobromination in aprotic polar solvents to give 2-imino-5-carboxymethylidene-4-oxazolidone. In the presence of dry hydrogen chloride in dimethylacetamide the oxazole ring undergoes dehydrobromination and isomerization to an imidazole ring with the formation of 5-carboxymethylidenehydantoin. Methyl α-bromofumarate monoureide is formed when the oxazole ring of 2-imino-5-bromocarbomethoxymethyl-4-oxazolidone is opened with alkali.

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Authors and Affiliations

  1. All-Union Scientific-Research Institute of Applied Biochemistry, 229014, Olaine

    I. K. Yurgevits, É. L. Kupche & U. Ya. Mikstais

Authors
  1. I. K. Yurgevits
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  2. É. L. Kupche
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  3. U. Ya. Mikstais
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 972–975, July, 1979.

The authors thank S.I. Zav'yalov, I. Ya. Shternberg, and I. P. Sekatsis for their participation in the discussion of this research.

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Yurgevits, I.K., Kupche, É.L. & Mikstais, U.Y. Heterocyclic compounds based on maleic acid monoureide. Chem Heterocycl Compd 15, 794–798 (1979). https://doi.org/10.1007/BF00473567

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  • DOI: https://doi.org/10.1007/BF00473567

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