Synthesis and characterization of novel benzoxazine-based arylidinyl succinimide derivatives

Abstract

ABSTRACT1,4-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 (23–42) were synthesized in moderate to good yields by the reaction of ethyl 2-(7-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate (22) 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 (32). 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.