A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization.
[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.
Aillaud
Isabelle
I
Laboratoire de Synthèse Organométallique et Molécules Bioactives, CNRS UMR 5181, Université Claude Bernard-Lyon I, ESCPE Lyon. 43, Bd du 11 Novembre 1918, 69622 Villeurbanne, France.
Bossharth
Emmanuel
E
Conreaux
David
D
Desbordes
Philippe
P
Monteiro
Nuno
N
Balme
Geneviève
G