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- Publisher
- de Gruyter
- Copyright
- ©2018 Walter de Gruyter GmbH, Berlin/Boston
- ISSN
- 0932-0776
- eISSN
- 1865-7117
- DOI
- 10.1515/znb-2018-0065
- Publisher site
- See Article on Publisher Site
Abstract
AbstractThe 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.
Journal
Zeitschrift für Naturforschung B – de Gruyter
Published: Oct 25, 2018