A two-step synthesis of ferrocenyl pyrazole and pyrimidine derivatives based on carbonylative Sonogashira coupling of iodoferrocene

A new method for the synthesis of 3-substituted-1-ferrocenyl-2-propyn-1-ones was developed involving carbonylative Sonogashira coupling of iodoferrocene with terminal acetylenes. New ferrocenyl 1,3,5-trisubstituted pyrazoles and 2,4,6-trisubstituted pyrimidines were obtained by the addition-cyclocondensation reaction of the alkynones with hydrazines and guanidinium salts, respectively. The products were obtained with moderate to excellent yields and were characterised with various spectroscopic methods (1H NMR, 13C NMR IR, MS).

Graphical abstractA new method for the synthesis of 3-substituted-1-ferrocenyl-2-propyn-1-ones was developed involving carbonylative Sonogashira coupling of iodoferrocene with terminal acetylenes. New ferrocenyl 1,3,5-trisubstituted pyrazoles and 2,4,6-trisubstituted pyrimidines were obtained by the addition-cyclocondensation reaction of the alkynones with hydrazines and guanidium salts, respectively.Figure optionsDownload full-size imageDownload as PowerPoint slide