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Synthesis 2010(10): 1741-1744  
DOI: 10.1055/s-0029-1218692
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© Georg Thieme Verlag Stuttgart ˙ New York

Practical One-Pot Syntheses of Regioisomeric Furan-Fused Pyridinones (and Quinolinones) from Common Precursors

Thierry Delaunaya, David Conreauxa, Emmanuel Bosshartha, Philippe Desbordesb, Nuno Monteiro*a, Geneviève Balme*a
a ICBMS, Institut de Chimie et Biochimie Moléculaire et Supramoléculaire, CNRS UMR 5246, Université Lyon 1, ESCPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France
Fax: +33(4)72431214; e-Mail: balme@univ-lyon1.fr; e-Mail: monteiro@univ-lyon1.fr;
b Bayer Crop Science, 14/20 rue Baizet, BP9163, 69623 Lyon Cedex 09, France
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Publication History

Received 15 January 2010
Publication Date:
09 March 2010 (online)

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Abstract

3-Alkynyl-4-methoxypyridin-2(1H)-ones undergo cyclization via divergent pathways when heated in acetic acid or triethyl­amine as reagent-solvent under microwave irradiation to furnish selectively furo[2,3-b]pyridin-4-ones or their regioisomeric furo[3,2-c]pyridin-4-ones, respectively. The same strategy applies to the synthesis of furoquinolinones.

Key words

annulation - furan - alkyne - cross-coupling reaction - microwave irradiation

    References

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