Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

Date

2016-01-01

Author

Kelgokmen, Yılmaz
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

121
views

0
downloads

A facile and efficient synthetic route to densely substituted alkynylpyridines via a Sonogashira approach is reported. When treated with terminal alkynes in the presence of 5 mol% PdCl2(PPh3)(2), 5 mol% CuI and excess Et3N in DMF at 65 degrees C, iodopyridines underwent Sonogashira coupling to afford alkynyl-substituted pyridines in good to excellent yields. The coupling reaction has been found to be general for a wide range of iodopyridines and terminal alkynes, and tolerated the presence of aliphatic, aromatic, heteroaromatic and ferrocenyl groups with electron-withdrawing and electron-donating substituents. This coupling approach could allow for the rapid construction of a library of functionalized alkynylpyridines of pharmacological interest.

Subject Keywords

Propargylic beta-enaminones, One-pot synthesis, Diels-alder reactions, Topoisomerase-i inhibition, Intramolecular cyclization, Polysubstituted pyridines, Regioselective synthesis, Oxidative aromatization, Heterocyclic azadienes

URI

https://hdl.handle.net/11511/35187

Journal

RSC ADVANCES

DOI

https://doi.org/10.1039/c5ra21701f

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach KARADENİZ, EDA; Zora, Metin; KILIÇASLAN, Nihan Zulay (2015-11-25) A facile and efficient synthetic route to arylpyridines is reported. When heated with boronic acids in the presence of 5 mol % PdCl2(PPh3)(2) and KHCO3 in 4:1 DMF/H2O solution at 110 degrees C, 5-iodopyridines have undergone Suzuki-Miyaura coupling reactions to afford 5-aryl-substituted pyridines in good to excellent yields. The coupling reaction has been found to be general for a broad range of iodopyridines and boronic acids, and demonstrated good tolerance to a variety of aliphatic, aromatic, heteroaroma...
Facile synthesis of iodopyridines from N-propargylic beta-enaminones via iodine-mediated electrophilic cyclization KARABIYIKOĞLU, Sedef; Kelgokmen, YILMAZ; Zora, Metin (2015-06-24) A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic beta-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization has been found to be general for a broad range of N-propargylic beta-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating subst...
Tungsten(VI) oxide supported rhodium nanoparticles: Highly active catalysts in hydrogen generation from ammonia borane Akbayrak, Serdar; Tonbul, Yalcin; Özkar, Saim (2021-04-01) Herein, we report the use of tungsten(VI) oxide (WO3) as support for Rh0 nanoparticles. The resulting Rh0/WO3 nanoparticles are highly active and stable catalysts in H2 generation from the hydrolysis of ammonia borane (AB). We present the results of our investigation on the particle size distribution, catalytic activity and stability of Rh0/WO3 catalysts with 0.5%, 1.0%, 2.0% wt. Rh loadings in the hydrolysis reaction. The results reveal that Rh0/WO3 (0.5% wt. Rh) is very promising catalyst providing a turn...
TFA catalyzed sequential amination/annulation/aromatization reaction of 2-propynyl-1.3-dicarbonyl compounds with amines: A new one-pot approach to functionalized pyrroles Demir, Ayhan Sıtkı; Aybey, Asuman; Kayalar, Metin (ARKAT USA, Inc., 2005-10-9) Highly flexible and efficient syntheses of 1,2,3,5-substituted pyrroles starting from 2-propynyl1,3-dicarbonyl compounds and amines are presented. TFA catalyzed formation of the pyrroles is suggested to proceed through sequential amination of the carbonyl compounds followed by regioselective 5-exo-dig cyclization of the enaminone intermediate and aromatization.
Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization Cetinkaya, Yasin; Balcı, Metin (2014-12-03) A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. ...

Citation Formats

Y. Kelgokmen and M. Zora, “Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach,” RSC ADVANCES, pp. 4608–4621, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35187.