Synthesis and characterization of novel benzoxazine-based arylidinyl succinimide derivatives

1,4-Benzoxazine skeleton holds substantial promise for further exploration owing to its immense pharmacological potential. In this pursuit, a series of 20 novel benzoxazine-based arylidinyl succinimide derivatives (<b>23</b>–<b>42</b>) were synthesized in moderate to good yields by the reaction of ethyl 2-(7-(2,5-dioxo-2,5-dihydro-1<i>H</i>-pyrrol-1-yl)-3-oxo-2<i>H</i>-benzo[<i>b</i>][1,4]oxazin-4(3<i>H</i>)-yl)acetate (<b>22</b>) with various aromatic aldehydes under Wittig reaction conditions in the presence of triphenylphosphine and ethanol. All these synthesized compounds were fully characterized from their spectral data (¹H, ¹³C, and ²D NMR, IR, UV, high-resolution mass spectroscopy (HRMS)) and further confirmed by X-ray crystallographic analysis of a representative compound (<b>32</b>). Antibacterial activity of obtained arylidinyl succinimide derivatives was evaluated against both Gram-positive and Gram-negative bacterial strains and were found to exhibit insignificant activity as compared to the reference.