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Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides

Andersson, Hans ; Almqvist, Fredrik and Olsson, Roger LU orcid (2007) In Organic Letters 9(7). p.1335-1337
Abstract

Figure presented 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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author
; and
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
volume
9
issue
7
pages
1335 - 1337
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:17328555
  • scopus:34147178870
ISSN
1523-7060
DOI
10.1021/ol070184n
language
English
LU publication?
no
id
3076406d-76ee-4cf3-be4d-daeadf537161
date added to LUP
2019-10-02 11:00:21
date last changed
2025-10-31 12:17:13
@article{3076406d-76ee-4cf3-be4d-daeadf537161,
  abstract     = {{<p>Figure presented 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.</p>}},
  author       = {{Andersson, Hans and Almqvist, Fredrik and Olsson, Roger}},
  issn         = {{1523-7060}},
  language     = {{eng}},
  month        = {{03}},
  number       = {{7}},
  pages        = {{1335--1337}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Organic Letters}},
  title        = {{Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides}},
  url          = {{http://dx.doi.org/10.1021/ol070184n}},
  doi          = {{10.1021/ol070184n}},
  volume       = {{9}},
  year         = {{2007}},
}