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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Orthoamide und Iminiumsalze, XCVa. Umsetzungen von Orthoamiden von Alkin-Carbonsäuren mit Acetophenonen und Acetophenon-Phenylhydrazonen

Orthoamides and iminium salts, XCVa. Reactions of alkynecarboxylic acid orthoamides with acetophenones and phenylhydrazones of acetophenones

Willi Kantlehner
  • Corresponding author
  • Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung (TOSKA), Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49(7361)5762250
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/ Jochen Mezger
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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/ Hansjörg Lehmann
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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/ Kai Edelmann
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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/ Wolfgang Frey
  • Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
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Published Online: 2018-09-13 | DOI: https://doi.org/10.1515/znb-2018-0065

Abstract

The orthoamides of alkyne carboxylic acids 4 react with acetophenones 5 – catalyzed by trialkylborates – to give ketene aminals 6, which can be transformed to 5-amino-5-hydrazino-penta-2,4-dien-1-ones 10 by treatment with 2,4-dinitro-phenylhydrazine. From acetophenone-phenylhydrazones 12 and orthoamides 4 1H-1,2-diazepines 18 (fett) are formed at room temperature, whereas 4-dimethylamino-pyridines 22 are obtained at elevated temperatures. The diazepine 18a is degraded to the pyridine-derivative 22b upon heating. The N-unsubstituted acetophenone-hydrazone 25 reacts with 4c to give amidrazone 26. The constitution of compounds 18a, 22a, 22b, 26 is established by crystal structure analyses.

Keywords: 1H-1,2-diazepines; 4-dimethylamino-pyridines; acetophenones; condensation reactions; crystal structure analysis; ketene aminals; orthoamides of alkyne carboxylic acids; phenylhydrazones

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About the article

aOrthoamide und Iminiumsalze XCIV: siehe Lit [1]


Received: 2018-03-19

Accepted: 2018-07-02

Published Online: 2018-09-13


Citation Information: Zeitschrift für Naturforschung B, 20180065, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0065.

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