Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers

Przemysslaw Frei; D. Heulyn Jones; Steven T. Kay; Jayde A. McLellan; Blair F. Johnston; Alan R. Kennedy; Nicholas C. O. Tomkinson

doi:10.1021/acs.joc.7b02457

Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers

Przemysslaw Frei, D. Heulyn Jones, Steven T. Kay, Jayde A. McLellan, Blair F. Johnston, Alan R. Kennedy, Nicholas C. O. Tomkinson

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Abstract

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.

Original language	English
Number of pages	8
Journal	Journal of Organic Chemistry
Early online date	18 Jan 2018
DOIs	https://doi.org/10.1021/acs.joc.7b02457
Publication status	E-pub ahead of print - 18 Jan 2018

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Keywords

N-oxides
heterocycles
nitrogen

Cite this

Frei, P., Jones, D. H., Kay, S. T., McLellan, J. A., Johnston, B. F., Kennedy, A. R., & Tomkinson, N. C. O. (2018). Regioselective reaction of heterocyclic N-oxides, an acyl chloride and cyclic thioethers. Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.7b02457

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abstract = "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.",

keywords = "N-oxides, heterocycles, nitrogen",

author = "Przemysslaw Frei and Jones, {D. Heulyn} and Kay, {Steven T.} and McLellan, {Jayde A.} and Johnston, {Blair F.} and Kennedy, {Alan R.} and Tomkinson, {Nicholas C. O.}",

note = "This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright {\circledC} 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.",

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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

JF - Journal of Organic Chemistry

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Access to Document

10.1021/acs.joc.7b02457

Frei-etal-JOC2018-Regioselective-reaction-of-heterocyclic-N-oxides-an-acyl-chlorideAccepted author manuscript, 1.06 MB

http://pubs.acs.org/journal/joceah