Synthesis and anodic electrochemistry of cymanquine and related complexes

• “Cymanquine”, the CpMn(CO)3 analogue of ferroquine, has been prepared.
• Anodic electrochemistry of cymanquine was recorded in a [B(C6F5)4]- - based electrolyte.
• The anodic oxidations of cymanquine are irreversible and involve its tertiary and secondary amines.

Three compounds have been prepared in which a 4-aminochloroquinoline moiety is covalently linked to a cyclopentadienyl manganese tricarbonyl moiety. One of these (“cymanquine”, 4) is the analogue of the potent antimalarial drug ferroquine in which an FeCp group has been replaced by a Mn(CO)3 group. The anodic electrochemistry of the new compounds was investigated in dichloromethane, using [NBu4][B(C6F5)4] as the supporting electrolyte. Compared to ferroquine, oxidations of the new compounds occur at considerably more positive potentials and are highly irreversible, being located at their amine groups rather than at the organometallic center.

Cymanquine, a direct analogue of ferroquine, has been prepared, along with two other closely-related MnCp(CO)3/4-aminochloroquinoline hybrid molecules. The most facile oxidation of the manganese compounds occurs at their aliphatic amine groups, rather than at the organometallic center.Figure optionsDownload as PowerPoint slide