Mechanochemical Synthesis and Isomerization of N-Substituted Indole-3-carboxaldehyde Oximes †.

ABSTRACT: Performing solution-phase oximation reactions with hydroxylamine hydrochloride (NH₂OH·HCl) carries significant risk, especially in aqueous solutions. In the present study, four N-substituted indole-3-carboxaldehyde oximes were prepared from the corresponding aldehydes by solvent-free reaction with NH₂OH·HCl and a base (NaOH or Na₂CO₃) using a mechanochemical approach, thus minimizing the possible risk. In all cases, the conversion to oximes was almost complete. The focus of this work is on 1-methoxyindole-3-carboxaldehyde oxime, a key intermediate in the production of indole phytoalexins with useful antimicrobial properties. Under optimized conditions, it was possible to reach almost 95% yield after 20 min of milling. Moreover, for the pro

SUBMITTER: Balaz M 

PROVIDER: S-EPMC6766794 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature