Synthesis of N‐Acyl Indole‐3‐Carboxaldehyde Derivatives and Polyvinyl Alcohol Acetalization with 1‐Propionylindole‐3‐Carboxaldehyde

Abstract

A series of seven stable amide derivatives based on indole‐3‐carboxaldehyde were synthesized with high yields using various aliphatic and aromatic acyl chlorides, triethylamine and DMAP as the catalyst at room temperature. Structural characterization was performed using FT‐IR, 1 H‐NMR, 13C‐NMR and LC–MS techniques. To develop bioactive material, acetalization of water‐soluble polyvinyl alcohol was achieved by reacting one of the N‐acyl derivatives, 1‐propionylindole‐3‐carboxaldehyde, in the presence of a p‐TSA catalyst to form polyvinyl acetal with pendant bioactive groups. The polymer was analyzed using 1 H‐NMR, FT‐IR, TGA, DSC, FE‐SEM and EDX spectroscopic techniques. The polymer was water‐insoluble with enhanced thermal stability compared to pure polyvinyl alcohol. This approach for developing N‐acyl derivatives of indole‐3‐carboxaldehyde and then reacting one of the monomers with polyvinyl alcohol to improve its thermal properties and stability in humid conditions has proven successful.