Synthesis, characterization, electronic absorption and antimicrobial studies of N-(silatranylpropyl)phthalimide derived from phthalic anhydride

•Transimidization reaction for the synthesis of N-(triethoxysilylpropyl)phthalimide.•Silatranes derived from phthalic anhydride possessing phthalimide as an exocyclic substituent.•Four routes for the synthesis N-(silatranylpropyl)phthalimide.•The electronic absorption and antimicrobial studies of N-(silatranylpropyl)phthalimide.

The transimidization reaction between phthalic anhydride and (3-aminopropyl)triethoxysilane was carried out using 2-(3-methylpyridin-2-yl)isoindoline-1,3-dione 1 to synthesize N-(triethoxysilylpropyl)phthalimide 2 in good yield. New silatranes 3 and 4 containing phthalimide as exocyclic group were prepared by the transesterification reactions of N-(triethoxysilylpropyl)phthalimide 2 with triethanolamine and trisisopropanolamine respectively. All the compounds were characterized by elemental analysis, spectroscopic techniques and thermogravimetric analysis. The compounds 3 and 4 were also characterized by X-ray diffraction analysis. The electronic absorption spectra of compounds 3 and 4 were studied in six solvents with different polarities. N-(silatranylpropyl)phthalimides were evaluated for the preliminary antimicrobial activity using broth microdilution method.

Graphical abstractN-(triethoxysilylpropyl)phthalimide 2 was synthesized by the transimidization reaction between phthalic anhydride and (3-aminopropyl)triethoxysilane using 2-(3-methylpyridin-2-yl)isoindoline-1,3-dione 1. The transesterification reaction of N-(triethoxysilylpropyl)phthalimide 2 with triethanolamine and trisisopropanolamine led to the synthesis of silatranes 3 and 4 respectively containing phthalimide as exocyclic group. The structures of compounds 3 and 4 were authenticated by X-ray diffraction analysis. The electronic absorption and antimicrobial studies of compounds 3 and 4 were also examined.Figure optionsDownload full-size imageDownload as PowerPoint slide