Synthesis of ferrocenyl substituted pyrazoles

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2005

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Görmen, Meral

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Pyrazoles have been studied for over a century as an important class of heterocyclic compounds and continue to attract considerable interest due to the broad range of biological activities they possess. The incorporation of the essential structural features of pyrazoles with a ferrocene moiety could provide new derivatives with unexpected and/or enhanced biological activities since several ferrocene derivatives have already been shown to be active against a number of tumors. For this reason, we investigated the synthesis of ferrocenyl-substituted pyrazoles, such as 1-alkyl/aryl-5-ferrocenylpyrazoles, by employing the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives. Although this reaction is known, it was not studied in much detail and the low yields of ferrocenyl pyrazoles were obtained. Thus, we have reinvestigated this reaction and improved the yields of pyrazoles by optimizing the reaction conditions. (2-Formyl-1-chloro vinyl)ferrocene was first reacted with the excess amount (3 equivalents) of hydrazine derivative at 25 0C in dioxane under argon for 2 hours, and the resulting mixture was then heated at 100 0C for 6 hours in the same solvent. Under our optimized conditions, these reactions afforded 1-alkyl/aryl-5-ferrocenylpyrazole derivatives in moderate to good yields as a single or major product of the reaction. In some cases, 1-alkyl/aryl-3-ferrocenylpyrazole derivatives resulted from these reactions as very minor products.

Subject Keywords

Alchemy.

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http://etd.lib.metu.edu.tr/upload/3/12606358/index.pdf
https://hdl.handle.net/11511/15200

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

M. Görmen, “Synthesis of ferrocenyl substituted pyrazoles,” M.S. - Master of Science, Middle East Technical University, 2005.