Synthesis of 2-Substituted Pyridines via a Regiospecific Alkylation, Alkynylation, and Arylation of Pyridine N-Oxides

Hans Andersson,† Fredrik Almqvist,*† and Roger Olsson*‡;
Department of Chemistry, Ume University, SE-901 87 Ume, Sweden, and ACADIA Pharmaceuticals AB, Medeon Science Park S-20512, Malm, Sweden
Org. Lett., 2007, 9 (7), pp 1335–1337
DOI: 10.1021/ol070184n
Publication Date (Web): March 1, 2007
Copyright © 2007 American Chemical Society
†

 Umeå University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 ACADIA Pharmaceuticals AB.

, fredrik.almqvist@chem.umu.se, ; , roger@acadia-pharm.com

Abstract

Abstract Image

Sequential addition of Grignard reagents to pyridine N-oxides in THF at room temperature followed by treatment with acetic anhydride at 120 °C afforded 2-substituted pyridines in good to high yields. Furthermore, by exchanging acetic anhydride for DMF in the second step, 2-substituted pyridine N-oxides were obtained, as intermediates suitable for addition of a second Grignard reagent for the synthesis of 2,6-disubstituted pyridines.

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History

  • Published In Issue March 29, 2007
  • Received January 24, 2007

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