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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  1 H -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.

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