One-pot synthesis of 2-ferrocenyl-substituted pyridines

Date

2016-11-02

Author

KARADENİZ, EDA
Zora, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

146
views

0
downloads

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

Suggestions

OpenMETU
Core

A New Strategy for the Synthesis of 4-Propargyl-Substituted 1H-Pyrroles from N-(5-phenyl-2,4-pentadiynyl) beta-Enaminones Yılmaz, Elif Serel; Zora, Metin (2019-10-09) A new method for the synthesis of 4-propargyl-substituted 1H-pyrroles is described. When treated with sodium hydride in refluxing dichloromethane, N-(5-phenyl-2,4-pentadiynyl) beta-enaminones, synthesized by the coupling of N-propargylic beta-enaminones with phenylacetylene, afforded 4-propargyl-substituted pyrrole derivatives. This conversion was general for a variety of N-(5-phenyl-2,4-pentadiynyl) beta-enaminones and displayed broad functional group tolerance. During the reaction, not only cyclization of...
One-pot synthesis of iodine-substituted 1,4-oxazepines Zora, Metin; KELGÖKMEN, YILMAZ (Elsevier BV, 2018-02-28) A facile one-pot method for the synthesis of iodine-substituted 1,4-oxazepines is reported. When reacted with ZnCl2 and I-2 in DCM at 40 degrees C, N-propargylic beta-enaminones, prepared by the conjugate addition of propargylamine to alpha,beta-alkynic ketones, underwent 7-exo-dig cyclization by zinc chloride and concomitant reaction with molecular iodine to afford 2-(iodomethylene)-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization was found to occur with broad scope of substrates and hig...
One-Pot Synthesis of Spiro-2H-pyrroles fromN-Propargylic beta-Enaminones KARADENİZ, EDA; Zora, Metin (Georg Thieme Verlag KG, 2019-06-01) A simple and general one-pot method for the synthesis of spiro-2 H -pyrroles has been developed. Initially, cyclohexane-embedded -enaminones with internal alkyne functionality were synthesized by conjugate addition of 1-ethynylcyclohexylamine to ,-alkynic ketones, followed by palladium-catalyzed coupling of the resulting N -propargylic -enaminones with aryl iodides. When subjected to basic conditions, the cyclohexane-embedded -enaminones with internal alkyne functionality underwent tandem nucleophilic cycli...
A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles Zora, Metin; Kelgokmen, YILMAZ (Elsevier BV, 2014-06-01) One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of 5-ferrocenyl-1,2,4-oxadiazole derivatives. The reaction first produces the corresponding conjugate addition product which, upon cyclization and rearrangement, yields the targeted 1,2,4-oxadiazole. The reaction appears to be general for a diversity of amidox...
A facile one-pot synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines Yılmaz, Elif Serel; Zora, Metin (Informa UK Limited, 2020-11-01) An unprecedented method for the synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines from N-(2,4-pentadiynyl) beta-enaminones is reported. Upon treatment with Lawesson's reagent, N-(2,4-pentadiynyl) beta-enaminones were thionated to furnish N-(2,4-pentadiynyl) beta-enaminothiones, which immediately underwent 7-exo-dig cyclization to generate 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines in one-pot. A general trend was observed for various N-(2,4-pentadiynyl) beta-enaminones and cyclization...

Citation Formats

E. KARADENİZ and M. Zora, “One-pot synthesis of 2-ferrocenyl-substituted pyridines,” TETRAHEDRON LETTERS, pp. 4930–4934, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47084.