Synthesis of Heteroarylferrocenes by FriedlanderReaction and Their Spectral Properties

Synthesis of Heteroarylferrocenes by FriedlanderReaction and Their Spectral Properties

A series of mono- and 1,1'-bis(heteroaryl)-substituted ferrocenes were prepared by employing Frielander reaction of acetyl- and 1,1'-diacetylferrocene with a series of o-aminoaldehydes. Reactions of 1,1'-diacetylferrocene with two equivalents of 1-aminonaphthalene-2-carbaldehyde and 8-aminoquinoline-7-carbaldehyde afforded a mixture of mono- and 1,1'-bis(heteroaryl)-substituted ferrocenes in a ratio of 1 : 3.1 - 3.8, while the reaction with 4-aminoacridine-3-carbaldehyde did not provide any characterizable product presumably due to the redox instability of the product induced by low reduction potential of benzo[b]-1,10-phenanthroline. Structural and optical properties of the compounds prepared were described.