Synthesis, characterization and antibacterial activity of some new ferrocenyl selenazoles and 3,5-diferrocenyl-1,2,4-selenadiazole

•A new series of novel ferrocene derivatives containing selenazole-moiety were synthesized.•Ferrocenyl selenocarboxamide and 3,5-diferrocenyl-1,2,4-selenadiazole were synthesized.•The new compounds showed potential biological activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa strains.

New ferrocenyl containing selenazole derivatives were synthesized from reactions of aryl selenocarboxamide (i.e. Ar–CSe(NH2); ArC6H5 (1), 4-Br-C6H4 (2), 4-PhC6H4 (3), 4-CH3OC6H4 (4), 4-CH3SC6H4 (5), 6-MeO–naphyl (6), 4-MeO–naphthyl (7), 4-C2H5OC6H4 (8), 3,4-(CH3O)2C6H3 (9), and 3,5-(CH3O)2C6H3 (10)) with (2-bromoacetyl)ferrocene. The structures of the new compounds were determined by elemental analyses, IR, 1H and 13C NMR and mass spectroscopic data.Reaction of 1-cyanoferrocene with sodium hydrogen selenide (NaHSe) in methanol gave the new ferrocenyl selenocarboxamide (11) in 27% yield. Treatment of compound 11 with a catalytic amount of Na2[PdCl4] gave 3,5-diferrocenyl-1,2,4-selenadiazole in 35% yield. Both compounds were characterized elemental analyses and spectroscopic techniques.Compounds 1–10 and 12 were screened as antibacterial agents against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa and showed promising properties.

Graphical abstractNew ferrocenyl containing selenazole derivatives, ferrocenyl selenocarboxamide and 3,5-diferrocenyl-1,2,4-selenadiazole were prepared and characterized by several spectroscopic techniques. The new compounds were screened as antibacterial agents against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa and showed promising properties.Figure optionsDownload full-size imageDownload as PowerPoint slide