Benzyl-N-phenylhydrazine derivatives of 1,3-diketones and 1,3-ketoesters undergo normal Fischer cyclisations to indoles, but no method could be found for the subsequent removal of the N-protecting group. No method could be found for the indolisation of N-aroyl-N-phenylhydrazine derivatives of dimedone with retention of the Nprotecting group, though heating in tetralin did effect the electrocyclic step of the Fischer sequence and the formation of a carbon-carbon bond.
Starting from 2,5‐bisarylidenecyclopentanone and malononitrile (1:1) several novel pyrindine derivatives were synthesized by a facile and convenient one‐pot reaction using sodium ethoxide in absolute ethanol at room temperature. The structure of the reaction products was unambiguously deduced ftom their infrared, 1H‐nuclear magnetic resonance spectroscopy, elemental analysis and single crystal X‐ray crystallography.
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Möglichkeiten einer Verhinderung der Pyrazol‐Bildung bei der Fischer‐Synthese der Titelverbindungen durch Einführung einer N‐Schutzgruppe werden untersucht.
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