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

A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic β-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization...

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Bibliographic Details
Published in:Tetrahedron 2015-06, Vol.71 (25), p.4324-4333
Main Authors: Karabiyikoglu, Sedef, Kelgokmen, Yilmaz, Zora, Metin
Format: Article
Language:English
Subjects:
Electrophilic cyclization
Iodocyclization
Iodopyridine
N-Propargylic β-enaminone
Pyridine
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Description
Summary:A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic β-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 β-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The starting N-propargylic β-enaminones have been prepared by conjugate addition of propargylamine to α,β-alkynic ketones, followed by Sonogashira coupling with aryl iodides. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.070