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Synthesis 2009(18): 3026-3028  
DOI: 10.1055/s-0029-1216894
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Furo[3,4-b]pyridin-5(7H)-ones from 2-Bromopyridine-3-carboxylic Acid and Carbonyl Compounds

Kazuhiro Kobayashi*, Taketoshi Kozuki, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 26 March 2009
Publication Date:
10 July 2009 (online)

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Abstract

A one-pot method for the preparation of furo[3,4-b]pyridine-5(7H)-ones from commercially available 2-bromopyridine-3-carboxylic acid has been developed. Thus, this acid is treated with two molar amounts of butyllithium to generate lithium 2-lithiopyridine-3-carboxylate, which is then allowed to react with carbonyl compounds to afford, after treatment with hydrochloric acid, the desired furopyridinones in reasonable yields.

Key words

furopyridinones - 2-bromopyridine-3-carboxylic acid - lithium 2-lithiopyridine-3-carboxylate - bromine-lithium exchange - lactonization

    References

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3

When the treatment of 1 with n-BuLi was prolonged to 10 min, only trace amounts of the desired products were obtained. The stability of this dilithium intermediate 2 could not be improved by using Et2O or DME in place of THF.