Synthesis and characterization of novel benzoxazine-based arylidinyl succinimide derivatives. Issue 20 (18th October 2017)

• Record Type: Journal Article
• Authors: Sharma, Atul K.; Prasad, Suchita; Sharma, Sunil K.
• Is Part Of: Synthetic communications. Volume 47:Issue 20(2017)
• Page Start: 1854
• Page End: 1863
• Publication Date: 2017-10-18
• Subjects: Antibacterial activity -- aromatic aldehyde -- arylidinyl succinimide -- benzoxazine; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2017.1354027
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: 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 (23 –42 ) were synthesized in moderate to good yields by the reaction of ethyl 2-(7-(2, 5-dioxo-2, 5-dihydro-1 H -pyrrol-1-yl)-3-oxo-2 H -benzo[ b ][1, 4]oxazin-4(3 H )-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 ( 1 H, 13 C, and 2 D 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. GRAPHICAL ABSTRACT: