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;
Further Information

Publication History

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

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.

    References

  • Generation of lithium 2-lithiobenzoate from 2-bromoben-zoic acid has been reported by Parham et al.:
  • 1a Parham WE. Piccirilli RM. J. Org. Chem.  1976,  41:  1268 
  • Its applications to the synthesis of phthalides have also been reported:
  • 1b Parham WE. Egberg DC. Sayed YA. Thrrailkill RW. Kaeyser GE. Neu M. Montgomery WC. Jones LD. J. Org. Chem.  1976,  41:  2628 
  • 1c Pirkle WH. Sowin TJ. J. Org. Chem.  1987,  52:  3011 
  • 2a Canonne P. Lemay G. Belanger D. Tetrahedron Lett.  1980,  21:  4167 
  • 2b Kende AS. Veits JE. Lorah DP. Ebetino FH. Tetrahedron Lett.  1984,  25:  2423 
  • 2c van Bergman TJ. Kellogg RM. J. Am. Chem. Soc.  1972,  94:  8451 
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.