A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization

Organic Letters
Isabelle AillaudGeneviève Balme

Abstract

[reaction: see text] N-Methyl-4-alkoxy-3-alkynylpyridin-2(1H)-ones readily undergo iodine-promoted 5-endo-heteroannulation under mild conditions to 3-iodofuropyridinium triiodide salts in moderate to good yields. The latter may be dealkylated in situ upon exposure to an iodide anion to provide the corresponding 3-iodofuro[2,3-b]pyridin-4(1H)-ones. The same strategy applies to the formation of furo[2,3-b]quinolin-4(9H)-ones.

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Feb 6, 2008·Natural Product Reports·Joseph P Michael
Mar 10, 2012·Organic & Biomolecular Chemistry·Ende LiYanzhong Li
Apr 6, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kyohei YonekuraTeruhisa Tsuchimoto
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Feb 4, 2010·The Journal of Organic Chemistry·Saurabh Mehta, Richard C Larock

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