One-pot synthesis of 2-ferrocenyl-substituted pyridines

Date

2016-11-02

Author

KARADENİZ, EDA
Zora, Metin

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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

Citation Formats

E. KARADENİZ and M. Zora, “One-pot synthesis of 2-ferrocenyl-substituted pyridines,” TETRAHEDRON LETTERS, vol. 57, no. 44, pp. 4930–4934, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47084.