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Zur Chemie des Maleinsäure-monoureides, 2. Mitt.: Reaktionen an der Doppelbindung der Maleinursäure

Maleic acid monoureide, II.: Reactions With the Double Bond of N-carbamoyl-maleamic acid

  • Organische Chemie und Biochemie
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Abstract

Electrolytic reduction of N-carbamoyl-maleamic acid and its N-alkyl derivatives (1 a-c) leads to mono-ureido-succinic acids in good yields, while alkylene-bis-N-carbamoyl-maleamic acids (3 a-e) are not attacked at the double bond under the same conditions. N-(Phenyl-carbamoyl)-maleamic acid (4) shows isomerisation to the fumaric acid derivative5 with pyridine, while NaOH causes cyclisation to an imidazolidine acetic acid6.

Addition of formaldehyde to N-carbamoyl-maleamic alkyl esters9 yields 3-carbamoyl-4-oxo-5-oxazolidine acetic acids (10 a-c).

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Author notes

  1. Harald Rauch-Puntigam

    Present address: Forschungsschwerpunkt Kunstharze und Lacke, Graz

Authors and Affiliations

  1. Institut für Organische Chemie, Abteilung für Organische Chemie I, Universität Graz, Heinrichstraße 28, A-3010, Graz, Österreich

    Hans Junek, Nicholas M. Jacobson, Peter Wiedner & Kurt Nordberg

  2. Forschungszentrum der Vianova-Kunstharz AG, Heinrichstra\e 28, A-8010, Graz, Österreich

    Harald Rauch-Puntigam

Authors
  1. Hans Junek
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  2. Nicholas M. Jacobson
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  3. Peter Wiedner
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  4. Kurt Nordberg
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  5. Harald Rauch-Puntigam
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Junek, H., Jacobson, N.M., Wiedner, P. et al. Zur Chemie des Maleinsäure-monoureides, 2. Mitt.: Reaktionen an der Doppelbindung der Maleinursäure. Monatshefte für Chemie 109, 395–404 (1978). https://doi.org/10.1007/BF00906358

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  • DOI: https://doi.org/10.1007/BF00906358

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