A new one-pot acid catalyzed synthetic methodology has been described for synthesis of aromatic imines. The reaction is carried out under microwave irradiation using minimum amount of methanol as solvent. Aqueous solution of the acid catalyst act as solvent for amine dissolution. The reaction yields substantial yield of product imine. The simplicity and environmentally benign nature of the process are the most notable features. The process can also be extended to include wide number of substrates. Product of the reaction can be isolated by simple procedure. The reaction can be carried out under mild conditions without heating to a higher temperature which eventually prevents the formation of nitrile byproducts in the reaction. Byproduct formation was significantly less during the reaction.
The impact of linezolid as an antibiotic against gram‐positive bacteria has inspired synthetic chemists to use oxazolidinones as substrate molecule in the synthesis of newer scaffolds with important pharmacological implication. The oxazolidin‐2‐ones are key intermediates in the synthesis of many interesting biologically active compounds. Design and synthesis of a new series of (S)‐4‐(4‐aminobenzyl)‐2‐oxazolidinone based multifunctional azetidinones were accomplished. Synthesis of the scaffolds was performed through a multi‐step reaction process involving protection of amine functional group, conversion of protected (S)‐4‐(4‐aminobenzyl)‐2‐oxazolidinone to its acetic acid derivative and then to acid chloride, and finally coupled with different substituted aromatic imines under mild reaction conditions in presence of an appropriate base. Structural characterization was carried out using conventional spectroscopic techniques. The compounds were screened for their antimicrobial activity against gram‐positive and gram‐negative bacteria and were found to possess better and promising antimicrobial property than some of the reported antimicrobial drugs like disulfonamide and tetracycline. Additionally, the scaffolds also exhibit prominent sensing property for divalent metal cations like Cu2+, Zn2+, and Ni2+, through fluorescence quenching effect.
Significant progress attained in sensor science in recent years has resulted in the development of highly efficient fluorescence probes for sensing metal ions. Fluorescent molecular probes based on (R)‐(−)‐4‐phenyl‐2‐oxazolidone are reported here. Fluorescence studies indicated that the molecular probe could be used successfully to sense divalent metal cations such as Cu2+, Co2+, Pb2+, and Zn2+. The addition of divalent metal cations to the molecular probe produced a specific interaction pattern under UV–visible and fluorescence spectroscopy. These molecules could detect metal cations using fluorescence quenching. Stern–Volmer plots were used to determine quenching rate coefficients, which were calculated to be 2 × 101, 1.06 × 103 and 7.39 × 102 M−1 s−1 for copper, cobalt, and zinc respectively. Calculation of limit of detection for heavy metal cations revealed that the reported molecular probes improved the limit of detection compared with available standard data. Limit of quantitation values were also well within the permissible range. The frontier energy gap of highest occupied molecular orbital to the lowest unoccupied molecular orbital was evaluated using the density functional theory approach and Gaussian 09 W software, which complemented the coordination of azetidinones with divalent metal ions.
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