Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

Date

2016-01-01

Author

Kelgokmen, Yılmaz
Zora, Metin

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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

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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.