Abstract
Language | English |
---|---|
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Early online date | 18 Jan 2018 |
DOIs | |
Publication status | E-pub ahead of print - 18 Jan 2018 |
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Keywords
- N-oxides
- heterocycles
- nitrogen
Cite this
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Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. / Frei, Przemysslaw; Jones, D. Heulyn; Kay, Steven T.; McLellan, Jayde A.; Johnston, Blair F.; Kennedy, Alan R.; Tomkinson, Nicholas C. O.
In: Journal of Organic Chemistry, 18.01.2018.Research output: Contribution to journal › Article
TY - JOUR
T1 - Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers
AU - Frei, Przemysslaw
AU - Jones, D. Heulyn
AU - Kay, Steven T.
AU - McLellan, Jayde A.
AU - Johnston, Blair F.
AU - Kennedy, Alan R.
AU - Tomkinson, Nicholas C. O.
N1 - This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b02457.
PY - 2018/1/18
Y1 - 2018/1/18
N2 - Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
AB - Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to 74% iso-lated yield. The transformation can also be accomplished with alternative nitrogen containing hetero-cycles including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
KW - N-oxides
KW - heterocycles
KW - nitrogen
UR - http://pubs.acs.org/journal/joceah
U2 - 10.1021/acs.joc.7b02457
DO - 10.1021/acs.joc.7b02457
M3 - Article
JO - Journal of Organic Chemistry
T2 - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
ER -