Synthesis of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles by electrophilic cyclization

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2011

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Karahan Dağ, Fulya

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Pyrazoles have been intensely studied in the design and synthesis of biologically active agents because they display considerable medicinal activities. Recent studies have shown that integration of a ferrocenyl unit with structural features of pyrazoles can result in the formation of the new products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been illustrated to be active against a number of tumors. Therefore, we have investigated the electrophilic cyclizations of the hydrazones to afford 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-substituted pyrazole derivatives. First, the requisite hydrazone derivatives were synthesized by the reactions of ferrocenyl propargyl aldehydes or ketones with a series of hydrazines. Then electrophilic cyclizations of these hydrazones were investigated by treating with 4-(nitrophenyl)sulfenyl chloride as electrophile. By employing these electrophilic cyclizations, a series of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles, 5-ferrocenyl-4-((4-nitrophenyl) sulfenyl)-3-methyl-1H-pyrazoles and 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-3-phenyl-1H-pyrazoles have been synthesized in moderate to good yields.

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Chemistry, Organic

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http://etd.lib.metu.edu.tr/upload/12613443/index.pdf
https://hdl.handle.net/11511/20667

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

F. Karahan Dağ, “Synthesis of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles by electrophilic cyclization,” M.S. - Master of Science, Middle East Technical University, 2011.