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Synthesis and properties of 5-ferrocenyl-1H-pyrazole-3-carbaldehydes |
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| Authors: | Alexey N Rodionov Alexander A Simenel Alexander A Korlyukov Svetlana M Peregudova Elena Yu Osipova |
| Institution: | a A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., 119991 GSP-1 Moscow, Russian Federation b Moscow State Mining University, 6 Leninsky Ave., Moscow 119991, Russian Federation c N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation |
| Abstract: | New ferrocene derivatives - ethyl esters of 1-aryl-5-ferrocenyl-1H-pyrazole-3-carboxylic acids were synthesized. The corresponding aldehydes were obtained from acid esters in two steps. The reductive amination reaction of 5-ferrocenyl-1-phenyl-1H-pyrazole-3-carbaldehyde was studied. Several of these compounds were investigated by cyclic voltammetry. All of them exhibited a reversible one-electron oxidation-reduction wave owing to the ferrocene-ferricinium redox couple with a positive shift (0.51-0.69 V) compared with that of ferrocene (0.46 V). The X-ray crystal structure of the ethyl ether 1-(3-chloro-2-fluorophenyl)-5-ferrocenyl-1H-pyrazole-3-carboxylic acid is also presented. |
| Keywords: | Ferrocene Pyrazoles Reductive amination Cyclic voltammetry X-ray structure determination |
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