Facile synthesis of iodopyridines from N-propargylic beta-enaminones via iodine-mediated electrophilic cyclization

Date

2015-06-24

Author

KARABIYIKOĞLU, Sedef
Kelgokmen, YILMAZ
Zora, Metin

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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 substituents. The starting N-propargylic beta-enaminones have been prepared by conjugate addition of propargylamine to alpha,beta-allcynic ketones, followed by Sonogashira coupling with aryl iodides.

Subject Keywords

Electrophilic cyclization, Pyridine, Lodopyridine, N-Propargylic beta-enaminone, Lodocyclization

URI

https://hdl.handle.net/11511/41186

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2015.04.070

Collections

Department of Chemistry, Article

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Citation Formats

S. KARABIYIKOĞLU, Y. Kelgokmen, and M. Zora, “Facile synthesis of iodopyridines from N-propargylic beta-enaminones via iodine-mediated electrophilic cyclization,” TETRAHEDRON, pp. 4324–4333, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41186.