Efficient Synthesis of Ferrocenylquinolines via the Friedländer Reaction
摘要:
Acylferrocenes 2a-c reacted with ortho-aminoarylaldehydes 1a-e via the Friedlander condensation reaction to afford the corresponding ferrocenylquinolines 3a-o in moderate yields in the presence of sodium ethoxide (30 mmol%) under mild reaction conditions. Under the same reaction conditions, 1,1'-diacetylferrocene 2d and 1,1'-dipropionylferrocene 2e reacted with ortho-aminoaldehydes 1a-e to afford the corresponding 1,1'-bis(substituted quinolin-2-yl) ferrocene derivatives 3p-t. The structures of compounds 3a-t were determined and characterized by infrared, H-1 NMR, mass spectrometry, and elemental analysis. The crystal structures of 3e and 3q were determined by x-ray crystallography.