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Aillaud I, Bossharth E, Conreaux D, et al. A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization. Org Lett. 2006;8(6):1113-6doi: 10.1021/ol053048w.
Aillaud, I., Bossharth, E., Conreaux, D., Desbordes, P., Monteiro, N., & Balme, G. (2006). A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization. Organic letters, 8(6), 1113-6. https://doi.org/10.1021/ol053048w
Aillaud, Isabelle, et al. "A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization." Organic letters vol. 8,6 (2006): 1113-6. doi: https://doi.org/10.1021/ol053048w
Aillaud I, Bossharth E, Conreaux D, Desbordes P, Monteiro N, Balme G. A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization. Org Lett. 2006 Mar 16;8(6):1113-6. doi: 10.1021/ol053048w. PMID: 16524281.
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Org Lett. 2006 Mar 16;8(6):1113-6. doi: 10.1021/ol053048w.

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

Organic letters

Isabelle Aillaud, Emmanuel Bossharth, David Conreaux, Philippe Desbordes, Nuno Monteiro, Geneviève Balme

Affiliations

  1. 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.

PMID: 16524281 DOI: 10.1021/ol053048w

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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