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One-pot synthesis of 2-ferrocenyl-substituted pyridines
Date
2016-11-02
Author
KARADENİZ, EDA
Zora, Metin
Metadata
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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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A facile, one-pot method for the synthesis of 2-ferrocenylpyridines is described. When reacted with propargylamine, alpha,beta-alkynic ketones produced N-propargylic beta-enaminones in situ, which, in the presence of copper(I) chloride, underwent electrophilic cyclization to afford 2-ferrocenylpyridine derivatives in good to high yields. This cyclization was found to be general for a variety of alpha,beta-alkynic ketones and tolerated the presence of aryl groups with electron-withdrawing and electron-donating substituents. The enrichment of the pyridine core with a ferrocenyl moiety, in addition to benzoyl groups, may offer potential for the synthesis of molecules of pharmacological interest.
Subject Keywords
Pyridine
,
Ferrocene
,
Propargylamine
,
alpha,beta-Alkynic ketone
,
N-Propargylic beta-enaminone
,
Electrophilic cyclization
URI
https://hdl.handle.net/11511/47084
Journal
TETRAHEDRON LETTERS
DOI
https://doi.org/10.1016/j.tetlet.2016.09.080
Collections
Department of Chemistry, Article