An efficient synthesis of ferrocenyl substituted 3-cyanopyridine derivatives under ultrasound irradiation

An efficient synthesis of 2-alkoxy-4-aryl-6-ferrocenyl-3-cyanopyridines via the condensation of ferrocenyl substituted chalcones with malononitrile in a freshly prepared sodium alkoxide solution under ultrasound irradiation was investigated. Especially noteworthy, the reaction of 1-ferrocenyl-3-(pyridin-2-yl)prop-2-ene-1-one with malononitrile afforded 2-alkoxy-4-pyridyl-6-ferrocenylpyridine, with the loss of CN group on the 3-position of pyridine ring was first observed.

Graphical abstractAn efficient tandem synthesis of 2-alkoxy-4-aryl-6-ferrocenyl-3-cyanopyridines via the condensation of ferrocenyl substituted chalcones with malononitrile in a freshly prepared sodium alkoxide solution under ultrasound irradiation was investigated. Especially noteworthy, the reaction of 1-ferrocenyl-3-(pyridin-2-yl)prop-2-ene-1-one with malononitrile interestingly afforded 2-alkoxy-4-pyridyl-6-ferrocenylpyridine, with the loss of CN group on the 3-position of pyridine ring was first observed.Figure optionsDownload full-size imageDownload as PowerPoint slide